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Journal articles on the topic 'Allyic substitution'

Author: Grafiati

Published: 2 November 2024

Last updated: 31 July 2025

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1

Yang, Shuang, and Xinqiang Fang. "Copper-catalyzed yne-allylic substitutions: concept and recent developments." Beilstein Journal of Organic Chemistry 20 (October 31, 2024): 2739–75. http://dx.doi.org/10.3762/bjoc.20.232.

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The catalytic (asymmetric) allylation and propargylation have been established as powerful strategies allowing access to enantioenriched α-chiral alkenes and alkynes. In this context, combining allylic and propargylic substitutions offers new opportunities to expand the scope of transition metal-catalyzed substitution reactions. Since its discovery in 2022, copper-catalyzed yne-allylic substitution has undergone rapid development and significant progress has been made using the key copper vinyl allenylidene intermediates. This review summarizes the developments and illustrates the influences o

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2

Hastings, Alan. "Substitution Rates Under Stabilizing Selection." Genetics 116, no. 3 (1987): 479–86. http://dx.doi.org/10.1093/genetics/116.3.479.

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ABSTRACT Allelic substitutions under stabilizing phenotypic selection on quantitative traits are studied in Monte Carlo simulations of 8 and 16 loci. The results are compared and contrasted to analytical models based on work of M. Kimura for two and "infinite" loci. Selection strengths of S = 4Nes approximately four (which correspond to reasonable strengths of selection for quantitative characters) can retard substitution rates tenfold relative to rates under neutrality. An important finding is a strong dependence of per locus substitution rates on the number of loci.

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3

Vilotijevic, Ivan, Markus Lange, and You Zi. "Latent (Pro)Nucleophiles in Enantioselective Lewis Base Catalyzed Allylic Substitutions." Synlett 31, no. 13 (2020): 1237–43. http://dx.doi.org/10.1055/s-0040-1707130.

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The use of latent nucleophiles, which are molecules that are not nucleophilic but can be activated to act as a nucleophile at an opportune time during the reaction, expands the scope of Lewis base catalyzed reactions. Here, we provide an overview of the concept and show examples of applications to N- and C-centered nucleophiles in allylic substitutions. N- and C-silyl compounds are superior latent (pro)nucleophiles in Lewis base catalyzed reactions with allylic fluorides in which the formation of the strong Si–F bond serves as the driving force for the reactions. The latent (pro)nucleophiles e

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4

Lopes Jesus, A. J., Cláudio M. Nunes, Gil A. Ferreira, Kiarash Keyvan, and R. Fausto. "Photochemical Generation and Characterization of C-Aminophenyl-Nitrilimines: Insights on Their Bond-Shift Isomers by Matrix-Isolation IR Spectroscopy and Density Functional Theory Calculations." Molecules 29, no. 15 (2024): 3497. http://dx.doi.org/10.3390/molecules29153497.

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The intriguing ability of C-phenyl-nitrilimine to co-exist as allenic and propargylic bond-shift isomers motivated us to investigate how substituents in the phenyl ring influence this behavior. Building on our previous work on the meta- and para-OH substitution, here we extended this investigation to explore the effect of the NH2 substitution. For this purpose, C-(4-aminophenyl)- and C-(3-aminophenyl)-nitrilimines were photogenerated in an argon matrix at 15 K by narrowband UV-light irradiation (λ = 230 nm) of 5-(4-aminophenyl)- and 5-(3-aminophenyl)-tetrazole, respectively. The produced nitri

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5

Bergbreiter, David E., Andrew Kippenberger, and Zhenqi Zhong. "Catalysis with palladium colloids supported in poly(acrylic acid)-grafted polyethylene and polystyrene." Canadian Journal of Chemistry 84, no. 10 (2006): 1343–50. http://dx.doi.org/10.1139/v06-076.

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Grafts of poly(acrylic acid) on polyethylene powder (PE-g-PAA) or polystyrene (PS-g-PAA) can be used to support Pd(0) crystallites that function like a homogeneous Pd(0) catalyst in some reactions. These Pd–PE-g-PAA catalysts were active in allylic substitution reactions in the presence of added phosphine ligand. A catalyst analogous to the Pd–PE-g-PAA powder catalyst on polystyrene (Pd–PS-g-PAA) was similarly active for allylic substitution and could also be used in Heck reactions at 80–100 °C in N,N-dimethylacetamide (DMA). Analysis of the product solutions for Pd leachate and a correlation

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6

Kang, Suk-Ku, Dae-Yeun Kim, Ryung-Kee Hong, and Pil-Su Ho. "Ruthenium-Catalyzed Allylic Substitution of Allylic Cyclic Carbonates." Synthetic Communications 26, no. 17 (1996): 3225–35. http://dx.doi.org/10.1080/00397919608004631.

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7

Shekhar, Shashank, Brian Trantow, Andreas Leitner, and John F. Hartwig. "Sequential Catalytic Isomerization and Allylic Substitution. Conversion of Racemic Branched Allylic Carbonates to Enantioenriched Allylic Substitution Products." Journal of the American Chemical Society 128, no. 36 (2006): 11770–71. http://dx.doi.org/10.1021/ja0644273.

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8

Boussonnière, Anne, Anne-Sophie Castanet, and Hélène Guyon. "Transition-Metal-Free Enantioselective Reactions of Organomagnesium Reagents Mediated by Chiral Ligands." Synthesis 50, no. 18 (2018): 3589–602. http://dx.doi.org/10.1055/s-0037-1610135.

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Organomagnesium reagents are among the most important reagents in organic chemistry because of their great utility in forming carbon–carbon bonds. Although most enantioselective reactions using these organometallics involve transmetalation, the past decade has witnessed impressive advances in direct chiral-ligand-mediated reactions of organomagnesiums. This short review presents an overview of these achievements in enantioselective nucleophilic additions and substitutions.1 Introduction2 Enantioselective Nucleophilic Additions2.1 Addition to C=O Bonds2.2 Addition to C=N Bonds2.3 Addition to C

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9

Tridib, Tripathy, Kolya Haradhan, and R. De B. "Reactions of the allylic substrate at a glance." Journal of Indian Chemical Society Vol. 90, Sep 2013 (2013): 1473–88. https://doi.org/10.5281/zenodo.5790913.

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Department of Chemistry, Midnapore College, Midnapore, Paschim Medinipur-721 101, West Bengal, India Department of Chemistry, Vidyasagar University, Midnapore, Paschim Medinipur-721 102, West Bengal, India <em>E-mail </em>: brdranjan@yahoo.com <em>Manuscript received 18 October 2012, accepted 02 November 2012</em> The chemistry of the allylic compounds has played, an important part in organic chemistry. Rearrangements in the allylic substrate have been long known. Allylic rearrangements are often observed in bimolecular (SN<sup>2</sup>) as well as in unimolecular substitution (SN<sup>1</sup>)

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10

Thoke, Mahesh Bhagwan, and Qiang Kang. "Rhodium-Catalyzed Allylation Reactions." Synthesis 51, no. 13 (2019): 2585–631. http://dx.doi.org/10.1055/s-0037-1611784.

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Rhodium-catalyzed allylation reactions are well known for their unique selectivity and reactivity due to the high memory effect of Rh as compared to other metals. These reactions involve the substitution of allylic rhodium intermediates with a diverse range of different nucleophiles, leading to C–C and C–heteroatom bond formation. Modern organic chemists are, however, interested in atom-economical protocols under greener pathways and following recent increased understanding of mechanistic aspects of Rh-catalyzed allylation via the hydrofunctionalization of allenes or alkynes, great strides hav

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11

Kojima, Masahiro, Shigeki Matsunaga, Tomoyuki Sekino та ін. "Allyl 4-Chlorophenyl Sulfone as a Versatile 1,1-Synthon for Sequential α-Alkylation/Cobalt-Catalyzed Allylic Substitution". Synthesis 52, № 13 (2020): 1934–46. http://dx.doi.org/10.1055/s-0040-1707524.

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Despite their unique potential as rare 1,1-dipole synthons, allyl sulfones are rarely used in target-oriented syntheses, likely due to the lack of a general catalytic method for their branch-selective allylic substitution. Herein, we identified allyl 4-chlorophenyl sulfone as a versatile linchpin for both base-mediated α-derivatization and subsequent cobalt-catalyzed allylic substitution. The sequential transformations allow for highly regioselective access to branched allylic substitution products with a variety of aliphatic side chains. The photoredox-enabled cobalt catalysis is indispensa

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12

Takeuchi, Ryo. "Iridium-Catalyzed Enantioselective Allylic Substitution." Journal of Synthetic Organic Chemistry, Japan 74, no. 9 (2016): 885–902. http://dx.doi.org/10.5059/yukigoseikyokaishi.74.885.

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13

Alexakis, A., and C. Falciola. "Copper-Catalyzed Asymmetric Allylic Substitution." Synfacts 2007, no. 7 (2007): 0714. http://dx.doi.org/10.1055/s-2007-968661.

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14

You, S. L., Q. L. Xu, W. B. Liu, and L. X. Dai. "Iridium-Catalyzed Asymmetric Allylic Substitution." Synfacts 2010, no. 10 (2010): 1161. http://dx.doi.org/10.1055/s-0030-1258691.

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15

Carreira, E., and M. Roggen. "Stereospecific Substitution of Allylic Alcohols." Synfacts 2010, no. 11 (2010): 1259. http://dx.doi.org/10.1055/s-0030-1258797.

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16

Malkov, Andrei V., Ian Baxendale, Darren J. Mansfield, and Pavel Kočovsky. "Molybdenum(II)-catalyzed allylic substitution." Tetrahedron Letters 38, no. 27 (1997): 4895–98. http://dx.doi.org/10.1016/s0040-4039(97)01052-6.

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17

Pfaltz, Andreas, and Mark Lautens. "ChemInform Abstract: Allylic Substitution Reactions." ChemInform 31, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.200018236.

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18

Crawley, M. L. "ChemInform Abstract: Allylic Substitution Reactions." ChemInform 42, no. 42 (2011): no. http://dx.doi.org/10.1002/chin.201142253.

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19

Han, Jun-Fa, Peng Guo, Xiang-Gui Zhang, Jia-Bin Liao, and Ke-Yin Ye. "Recent advances in cobalt-catalyzed allylic functionalization." Organic & Biomolecular Chemistry 18, no. 39 (2020): 7740–50. http://dx.doi.org/10.1039/d0ob01581d.

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20

Kim, Minjae, Gwanggyun Kim, Doyoon Kim, Jun Hee Lee, and Seung Hwan Cho. "Recent advances in allylation of chiral secondary alkylcopper species." Beilstein Journal of Organic Chemistry 21 (March 20, 2025): 639–58. https://doi.org/10.3762/bjoc.21.51.

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The transition-metal-catalyzed asymmetric allylic substitution represents a pivotal methodology in organic synthesis, providing remarkable versatility for complex molecule construction. Particularly, the generation and utilization of chiral secondary alkylcopper species have received considerable attention due to their unique properties in stereoselective allylic substitution. This review highlights recent advances in copper-catalyzed asymmetric allylic substitution reactions with chiral secondary alkylcopper species, encompassing several key strategies for their generation: stereospecific tra

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21

Butt, Nicholas A., and Wanbin Zhang. "Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates." Chemical Society Reviews 44, no. 22 (2015): 7929–67. http://dx.doi.org/10.1039/c5cs00144g.

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22

Bruneau, Christian, Jean-Luc Renaud, and Bernard Demerseman. "Ruthenium catalysts for selective nucleophilic allylic substitution." Pure and Applied Chemistry 80, no. 5 (2008): 861–71. http://dx.doi.org/10.1351/pac200880050861.

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Recent developments in the chemistry of η3-allylruthenium(IV) complexes are due to their straightforward synthesis resulting from oxidative addition of allylic substrates to a ruthenium(II) center. Subsequent reaction with a nucleophile is the basis of their involvement in the catalytic allylic substitution reaction. We focus here on ruthenium-catalyzed substitution of allylic substrates by C-, N-, and O-nucleophiles and show that selected ligands make regio- and enantioselective reactions possible.

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23

Bourgeois, Marie-Josèphe, Marianne Vialemaringe, Monique Campagnole, and Evelyne Montaudon. "Réaction compétitive de la substitution homolytique intramoléculaire : décomposition de peroxydes allyliques dans le thioglycolate de méthyle." Canadian Journal of Chemistry 79, no. 3 (2001): 257–62. http://dx.doi.org/10.1139/v01-024.

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The decomposition of allylic peroxides in methyl thioglycolate always leads to both epoxide and adduct peroxide. According to the nature of the allylic chain, either epoxide or peroxide is the predominant product, if not the only one. It is the first example where the hydrogen transfer is as fast as the intramolecular homolytic substitution. The influence of different factors upon the competition is studied.Key words: allylic peroxides, epoxides, intramolecular homolytic substitution, transfer.

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24

Busfield, WK, DI Grice, ID Jenkins, and SH Thang. "Reaction of t-Butoxy Radicals With Cyclic Alkenes Studied by the Nitroxide Radical-Trapping Technique." Australian Journal of Chemistry 44, no. 10 (1991): 1407. http://dx.doi.org/10.1071/ch9911407.

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The pattern of reactions occurring between t- butoxy radicals and a number of cyclic alkenes has been investigated by the nitroxide radical-trapping technique. The major reaction pathway is allylic abstraction unless this position is at a bridgehead as in norbornene where the major pathway is radical addition. The technique is sufficiently sensitive to identify minor reaction pathways of non-allylic substitution and radical addition when in the presence of extensive allylic substitution. Some stereoselective effects are also detected.

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25

Kim, Byeong-Seon, Mahmud M. Hussain, Per-Ola Norrby, and Patrick J. Walsh. "Breaking conjugation: unusual regioselectivity with 2-substituted allylic substrates in the Tsuji–Trost reaction." Chem. Sci. 5, no. 3 (2014): 1241–50. http://dx.doi.org/10.1039/c3sc53035c.

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26

Kawatsura, Motoi, Maki Minakawa, and Toshiyuki Itoh. "Ruthenium-Catalyzed Stereoselective Allylic Substitutions." Journal of Synthetic Organic Chemistry, Japan 74, no. 1 (2016): 45–55. http://dx.doi.org/10.5059/yukigoseikyokaishi.74.45.

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27

Reiser, Oliver. "Palladium-Catalyzed, Enantioselective Allylic Substitutions." Angewandte Chemie International Edition in English 32, no. 4 (1993): 547–49. http://dx.doi.org/10.1002/anie.199305471.

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28

Starý, Ivo, Irena G. Stará, and Pavel Kocˇovský. "Palladium(O)-catalyzed allylic substitution with allylic alkoxides as substrates." Tetrahedron 50, no. 2 (1994): 529–37. http://dx.doi.org/10.1016/s0040-4020(01)80774-2.

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29

KANG, S. K., D. Y. KIM, R. K. HONG, and P. S. HO. "ChemInform Abstract: Ruthenium-Catalyzed Allylic Substitution of Allylic Cyclic Carbonates." ChemInform 27, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199648088.

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30

Zemtsov, Artem A., Vitalij V. Levin, and Alexander D. Dilman. "Allylic substitution reactions with fluorinated nucleophiles." Coordination Chemistry Reviews 459 (May 2022): 214455. http://dx.doi.org/10.1016/j.ccr.2022.214455.

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31

Alexakis, Alexandre, Christophe Malan, Louise Lea, Karine Tissot-Croset, Damien Polet, and Caroline Falciola. "The Copper-Catalyzed Asymmetric Allylic Substitution." CHIMIA International Journal for Chemistry 60, no. 3 (2006): 124–30. http://dx.doi.org/10.2533/000942906777674994.

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32

Pàmies, O., M. Diéguez, E. Raluy, and C. Claver. "Phosphoramidite-Phosphite Ligands for Allylic Substitution." Synfacts 2007, no. 4 (2007): 0395. http://dx.doi.org/10.1055/s-2007-968365.

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33

Cheng, Qiang, Hang-Fei Tu, Chao Zheng, Jian-Ping Qu, Günter Helmchen, and Shu-Li You. "Iridium-Catalyzed Asymmetric Allylic Substitution Reactions." Chemical Reviews 119, no. 3 (2018): 1855–969. http://dx.doi.org/10.1021/acs.chemrev.8b00506.

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34

Malkov, Andrei V., Paul Spoor, Victoria Vinader, and Pavel Kočovský. "Asymmetric molybdenum(0)-catalyzed allylic substitution." Tetrahedron Letters 42, no. 3 (2001): 509–12. http://dx.doi.org/10.1016/s0040-4039(00)02007-4.

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35

Hyodo, Tomonori, Yuji Katayama, and Yuichi Kobayashi. "Allylic substitution on the pyran ring." Tetrahedron Letters 50, no. 26 (2009): 3547–49. http://dx.doi.org/10.1016/j.tetlet.2009.03.018.

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36

Frost, Christopher G., Joshua Howarth, and J. M. J. Williams. "Selectivity in palladium catalysed allylic substitution." Tetrahedron: Asymmetry 3, no. 9 (1992): 1089–122. http://dx.doi.org/10.1016/s0957-4166(00)82091-1.

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37

Benedetto, Elena, Massaba Keita, Matthew Tredwell, Charlotte Hollingworth, John M. Brown, and Véronique Gouverneur. "Platinum-Catalyzed Substitution of Allylic Fluorides." Organometallics 31, no. 4 (2012): 1408–16. http://dx.doi.org/10.1021/om201029m.

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38

Hartwig, John F., and Mark J. Pouy. "ChemInform Abstract: Iridium-Catalyzed Allylic Substitution." ChemInform 42, no. 52 (2011): no. http://dx.doi.org/10.1002/chin.201152252.

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39

Hazari, Amaruka, Véronique Gouverneur, and John M Brown. "Palladium-Catalyzed Substitution of Allylic Fluorides." Angewandte Chemie International Edition 48, no. 7 (2009): 1296–99. http://dx.doi.org/10.1002/anie.200804310.

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40

Hazari, Amaruka, Véronique Gouverneur, and John M Brown. "Palladium-Catalyzed Substitution of Allylic Fluorides." Angewandte Chemie 121, no. 7 (2009): 1322–25. http://dx.doi.org/10.1002/ange.200804310.

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41

Purdue, P. E., Y. Takada, and C. J. Danpure. "Identification of mutations associated with peroxisome-to-mitochondrion mistargeting of alanine/glyoxylate aminotransferase in primary hyperoxaluria type 1." Journal of Cell Biology 111, no. 6 (1990): 2341–51. http://dx.doi.org/10.1083/jcb.111.6.2341.

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We have previously shown that in some patients with primary hyperoxaluria type 1 (PH1), disease is associated with mistargeting of the normally peroxisomal enzyme alanine/glyoxylate aminotransferase (AGT) to mitochondria (Danpure, C.J., P.J. Cooper, P.J. Wise, and P.R. Jennings. J. Cell Biol. 108:1345-1352). We have synthesized, amplified, cloned, and sequenced AGT cDNA from a PH1 patient with mitochondrial AGT (mAGT). This identified three point mutations that cause amino acid substitutions in the predicted AGT protein sequence. Using PCR and allele-specific oligonucleotide hybridization, a r

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42

Zhu, Xu, and Shunsuke Chiba. "TEMPO-mediated allylic C–H amination with hydrazones." Org. Biomol. Chem. 12, no. 26 (2014): 4567–70. http://dx.doi.org/10.1039/c4ob00839a.

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TEMPO-mediated reactions of alkenyl hydrazones afforded azaheterocycles via sp<sup>3</sup> C–H allylic amination. The transformation is featured by a sequence of remote allylic H-radical shift and allylic homolytic substitution with hydrazone radicals.

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43

Xu, Ruigang, Kai Li, Jiaqi Wang, et al. "Direct enantioselective allylic substitution of 4-hydroxycoumarin derivatives with branched allylic alcohols via iridium catalysis." Chemical Communications 56, no. 60 (2020): 8404–7. http://dx.doi.org/10.1039/d0cc02832k.

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An iridium catalysed direct asymmetric allylic substitution reaction of 4-hydroxycoumarin derivatives with allylic alcohols with remarkably high yields and excellent enantioselectivities was realized.

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44

Kobayashi, Yuichi, and Takuri Ozaki. "Concise Synthesis of (–)-Axenol by Using Stereocontrolled Allylic Substitution." Synlett 26, no. 08 (2015): 1085–88. http://dx.doi.org/10.1055/s-0034-1380273.

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Synthesis of (–)-axenol was achieved stereoselectively through allylic substitution to form the quaternary carbon followed by ring-closing metathesis. The key allylic picolinate was synthesized from natural menthol.

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45

Xue, Weichao, and Martin Oestreich. "Silicon Grignard Reagents as Nucleophiles in Transition-Metal-Catalyzed Allylic Substitution." Synthesis 51, no. 01 (2018): 233–39. http://dx.doi.org/10.1055/s-0037-1610309.

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A broad range of transition-metal catalysts is shown to promote allylic substitution reactions of allylic electrophiles with silicon Grignard reagents. The procedure was further elaborated for CuI as catalyst. The regioselectively is independent of the leaving group for primary allylic precursors, favoring α over γ. The stereochemical course of this allylic transposition was probed with a cyclic system, and anti-diastereoselectivity was obtained.

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46

Liang, Xiao, Kun Wei та Yu-Rong Yang. "Iridium-catalyzed enantioselective allylation of silyl enol ethers derived from ketones and α,β-unsaturated ketones". Chemical Communications 51, № 98 (2015): 17471–74. http://dx.doi.org/10.1039/c5cc07221b.

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47

Sundararaju, Basker, Mathieu Achard та Christian Bruneau. "Transition metal catalyzed nucleophilic allylic substitution: activation of allylic alcohols via π-allylic species". Chemical Society Reviews 41, № 12 (2012): 4467. http://dx.doi.org/10.1039/c2cs35024f.

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48

Deng, Yingying, Wen Yang, Xin Yang, and Dingqiao Yang. "Progress in Iridium-Catalyzed Asymmetric Allylic Substitution Reactions with Allylic Esters." Chinese Journal of Organic Chemistry 37, no. 12 (2017): 3039. http://dx.doi.org/10.6023/cjoc201704034.

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49

Ma, Xiantao, Jing Yu, Zilong Wang, Yun Zhang, and Qiuju Zhou. "Efficient Activation of Allylic Alcohols in Pd-Catalyzed Allylic Substitution Reactions." Chinese Journal of Organic Chemistry 40, no. 9 (2020): 2669. http://dx.doi.org/10.6023/cjoc202005013.

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50

Kinouchi, Wataru, Ryohei Saeki, Hidehisa Kawashima, and Yuichi Kobayashi. "Palladium-catalyzed allylic substitution of secondary allylic esters with ketone enolates." Tetrahedron Letters 56, no. 17 (2015): 2265–68. http://dx.doi.org/10.1016/j.tetlet.2015.03.063.

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