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Journal articles on the topic 'Cross-electrophile coupling'

Author: Grafiati
Published: 4 June 2021
Last updated: 7 July 2024

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1

Völler, Jan-Stefan. "Photoenzymatic cross-electrophile coupling." Nature Catalysis 5, no. 9 (2022): 748. http://dx.doi.org/10.1038/s41929-022-00849-5.

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2

Shu, Xing-Zhong, Xiaobo Pang, and Xuejing Peng. "Reductive Cross-Coupling of Vinyl Electrophiles." Synthesis 52, no. 24 (2020): 3751–63. http://dx.doi.org/10.1055/s-0040-1707342.

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The synthesis of alkenes (olefins) is a central subject in the synthetic community. The transition-metal-catalyzed reductive cross-coupling of vinyl electrophiles has emerged as a promising tool to produce alkenes with improved flexibility, structural complexity, and functionality tolerance. In this review, we summarized the progress in this field with respect to cross-electrophile couplings and reductive Heck reactions using vinyl electrophiles.1 Introduction2 Cross-Electrophile Coupling of Vinyl Electrophiles3 Reductive Heck Reaction of Vinyl Electrophiles4 Summary and Outlook
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3

Li, Yangyang, Yuqiang Li, Long Peng, Dong Wu, Lei Zhu, and Guoyin Yin. "Nickel-catalyzed migratory alkyl–alkyl cross-coupling reaction." Chemical Science 11, no. 38 (2020): 10461–64. http://dx.doi.org/10.1039/d0sc03217d.

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4

Wang, Chuan, and Youxiang Jin. "Nickel-Catalyzed Asymmetric Cross-Electrophile Coupling Reactions." Synlett 31, no. 19 (2020): 1843–50. http://dx.doi.org/10.1055/s-0040-1707216.

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The merger of cross-electrophile coupling and asymmetric catalysis provides a novel approach to the preparation of optically active compounds. This method is often endowed with high step economy, mild conditions, and excellent tolerance of functional groups. Recent advances in the research field of nickel-catalyzed asymmetric cross-electrophile coupling reactions are highlighted in this concise Synpacts article.1 Introduction2 Asymmetric Cross-Electrophile Coupling Reactions between Organohalides3 Asymmetric Electrophilic Ring-Opening Reactions4 Asymmetric Electrophilic Difunctionalization of
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5

Jones, Andrew C., William I. Nicholson, Jamie A. Leitch, and Duncan L. Browne. "A Ball-Milling-Enabled Cross-Electrophile Coupling." Organic Letters 23, no. 16 (2021): 6337–41. http://dx.doi.org/10.1021/acs.orglett.1c02096.

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6

Sakai, Holt A., Wei Liu, Chi “Chip” Le, and David W. C. MacMillan. "Cross-Electrophile Coupling of Unactivated Alkyl Chlorides." Journal of the American Chemical Society 142, no. 27 (2020): 11691–97. http://dx.doi.org/10.1021/jacs.0c04812.

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7

Hanna, Luke E., and Elizabeth R. Jarvo. "Selective Cross-Electrophile Coupling by Dual Catalysis." Angewandte Chemie International Edition 54, no. 52 (2015): 15618–20. http://dx.doi.org/10.1002/anie.201509444.

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8

Yu, Hang, and Zhong-Xia Wang. "Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols." Organic & Biomolecular Chemistry 19, no. 44 (2021): 9723–31. http://dx.doi.org/10.1039/d1ob01874d.

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9

Zhang, Wen, Lingxiang Lu, Wendy Zhang, et al. "Electrochemically driven cross-electrophile coupling of alkyl halides." Nature 604, no. 7905 (2022): 292–97. http://dx.doi.org/10.1038/s41586-022-04540-4.

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10

Zhu, Dunming, and Ling Hua. "Photobiocatalysis enables asymmetric Csp3–Csp3 cross-electrophile coupling." Chem Catalysis 2, no. 10 (2022): 2429–31. http://dx.doi.org/10.1016/j.checat.2022.09.041.

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11

Everson, Daniel A., and Daniel J. Weix. "Cross-Electrophile Coupling: Principles of Reactivity and Selectivity." Journal of Organic Chemistry 79, no. 11 (2014): 4793–98. http://dx.doi.org/10.1021/jo500507s.

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12

Kölmel, Dominik K., Anokha S. Ratnayake, and Mark E. Flanagan. "Photoredox cross-electrophile coupling in DNA-encoded chemistry." Biochemical and Biophysical Research Communications 533, no. 2 (2020): 201–8. http://dx.doi.org/10.1016/j.bbrc.2020.04.028.

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13

Pan, Yingying, Yuxin Gong, Yanhong Song, Weiqi Tong, and Hegui Gong. "Deoxygenative cross-electrophile coupling of benzyl chloroformates with aryl iodides." Organic & Biomolecular Chemistry 17, no. 17 (2019): 4230–33. http://dx.doi.org/10.1039/c9ob00628a.

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14

Sha, Yunfei, Jiandong Liu, Liang Wang, Demin Liang, Da Wu, and Hegui Gong. "Nickel-catalyzed reductive 1,3-diene formation from the cross-coupling of vinyl bromides." Organic & Biomolecular Chemistry 19, no. 22 (2021): 4887–90. http://dx.doi.org/10.1039/d1ob00791b.

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15

Jarvo, Elizabeth R., Erika L. Lucas, Tristan M. McGinnis, and Anthony J. Castro. "Nickel-Catalyzed Cross-Electrophile Coupling of the Difluoromethyl Group for Fluorinated Cyclopropane Synthesis." Synlett 32, no. 15 (2021): 1525–30. http://dx.doi.org/10.1055/s-0040-1706013.

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AbstractHerein, we report a new strategy for fluorinated cyclopropane synthesis. Photocatalytic olefin difluoromethylation is coupled with a nickel-catalyzed intramolecular cross-electrophile coupling (XEC) reaction between a difluoromethyl moiety and a benzylic ether. To the best of our knowledge, this is the first example of a XEC reaction employing a difluoromethyl group as an electrophile. A plausible mechanism is highlighted, and DFT calculations are included to support the observed stereochemical outcome.
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16

Lin, Tingzhi, Jianjun Mi, Lichao Song, et al. "Nickel-Catalyzed Desymmetrizing Cross-Electrophile Coupling of CyclicMeso-Anhydrides." Organic Letters 20, no. 4 (2018): 1191–94. http://dx.doi.org/10.1021/acs.orglett.8b00114.

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17

Johnson, Keywan A., Soumik Biswas, and Daniel J. Weix. "Cross-Electrophile Coupling of Vinyl Halides with Alkyl Halides." Chemistry - A European Journal 22, no. 22 (2016): 7399–402. http://dx.doi.org/10.1002/chem.201601320.

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18

Hanna, Luke E., and Elizabeth R. Jarvo. "ChemInform Abstract: Selective Cross-Electrophile Coupling by Dual Catalysis." ChemInform 47, no. 8 (2016): no. http://dx.doi.org/10.1002/chin.201608251.

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19

Wu, Sisi, Weijia Shi, and Gang Zou. "Mechanical metal activation for Ni-catalyzed, Mn-mediated cross-electrophile coupling between aryl and alkyl bromides." New Journal of Chemistry 45, no. 25 (2021): 11269–74. http://dx.doi.org/10.1039/d1nj01732b.

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20

Buchspies, Jonathan, and Michal Szostak. "Recent Advances in Acyl Suzuki Cross-Coupling." Catalysts 9, no. 1 (2019): 53. http://dx.doi.org/10.3390/catal9010053.

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Acyl Suzuki cross-coupling involves the coupling of an organoboron reagent with an acyl electrophile (acyl halide, anhydride, ester, amide). This review provides a timely overview of the very important advances that have recently taken place in the acylative Suzuki cross-coupling. Particular emphasis is directed toward the type of acyl electrophiles, catalyst systems and new cross-coupling partners. This review will be of value to synthetic chemists involved in this rapidly developing field of Suzuki cross-coupling as well as those interested in using acylative Suzuki cross-coupling for the sy
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21

Ye, Ning, Bin Wu, Kangming Zhao, et al. "Micelle enabled C(sp2)–C(sp3) cross-electrophile coupling in water via synergistic nickel and copper catalysis." Chemical Communications 57, no. 62 (2021): 7629–32. http://dx.doi.org/10.1039/d1cc02885e.

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22

Wu, Fan, Wei Wang, and Ken Yao. "Nickel-Catalyzed Reductive Cross-Coupling of Benzylic Sulfonium Salts with Aryl Iodides." Synlett 33, no. 04 (2022): 361–66. http://dx.doi.org/10.1055/s-0041-1737762.

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A nickel-catalyzed cross-electrophile coupling of benzylic sulfonium salts with aryl iodides has been developed, providing direct access to diarylalkanes from readily available and stable coupling partners. Preliminary mechanistic studies suggest that the C–S bond cleavage proceeds through a single-electron transfer process to generate a benzylic radical.
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23

Ackerman, Laura K. G., Lukiana L. Anka-Lufford, Marina Naodovic, and Daniel J. Weix. "Correction: Cobalt co-catalysis for cross-electrophile coupling: diarylmethanes from benzyl mesylates and aryl halides." Chemical Science 6, no. 6 (2015): 3633. http://dx.doi.org/10.1039/c5sc90021b.

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24

Ackerman, Laura K. G., Lukiana L. Anka-Lufford, Marina Naodovic, and Daniel J. Weix. "Further correction: Cobalt co-catalysis for cross-electrophile coupling: diarylmethanes from benzyl mesylates and aryl halides." Chemical Science 8, no. 2 (2017): 1667. http://dx.doi.org/10.1039/c6sc90082h.

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25

Gao, Nanxing, Yanshun Li, and Dawei Teng. "Nickel-catalysed cross-electrophile coupling of aryl bromides and primary alkyl bromides." RSC Advances 12, no. 6 (2022): 3569–72. http://dx.doi.org/10.1039/d2ra00010e.

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The structure of primary alkylated arenes play an important role in the molecular action of drugs and natural products. The nickel/spiro-bidentate-pyox catalysed cross-electrophile coupling of aryl bromides and primary alkyl bromides was developed.
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26

Wang, Jiabao, Yuxin Gong, Deli Sun, and Hegui Gong. "Nickel-catalyzed reductive benzylation of tertiary alkyl halides with benzyl chlorides and chloroformates." Organic Chemistry Frontiers 8, no. 12 (2021): 2944–48. http://dx.doi.org/10.1039/d1qo00264c.

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We report a Ni-catalyzed cross-electrophile coupling of benzyl chlorides and chloroformates with unactivated tertiary alkyl halides to forge the challenging benzylated all C(sp<sup>3</sup>)-quaternary carbon centers.
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27

Salman, Muhammad, Yaoyao Xu, Shahid Khan, Junjie Zhang, and Ajmal Khan. "Regioselective molybdenum-catalyzed allylic substitution of tertiary allylic electrophiles: methodology development and applications." Chemical Science 11, no. 21 (2020): 5481–86. http://dx.doi.org/10.1039/d0sc01763a.

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The first general example of Mo-catalyzed allylic sulfonylation of tertiary allylic electrophile provides an efficient way to forge sulfone moieties, and providing ample opportunities for further transformation through traditional Suzuki cross-coupling.
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28

Charboneau, David J., Haotian Huang, Emily L. Barth, et al. "Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling." Journal of the American Chemical Society 143, no. 49 (2021): 21024–36. http://dx.doi.org/10.1021/jacs.1c10932.

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29

Jin, Youxiang, Hao Wen, Feiyan Yang, Decai Ding, and Chuan Wang. "Synthesis of Multisubstituted Allenes via Nickel-Catalyzed Cross-Electrophile Coupling." ACS Catalysis 11, no. 21 (2021): 13355–62. http://dx.doi.org/10.1021/acscatal.1c04143.

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30

Zackasee, Jordan L. S., Samir Al Zubaydi, Blaise L. Truesdell, and Christo S. Sevov. "Synergistic Catalyst–Mediator Pairings for Electroreductive Cross-Electrophile Coupling Reactions." ACS Catalysis 12, no. 2 (2022): 1161–66. http://dx.doi.org/10.1021/acscatal.1c05144.

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31

Smith, Russell T., Xiaheng Zhang, Juan A. Rincón, et al. "Metallaphotoredox-Catalyzed Cross-Electrophile Csp3–Csp3 Coupling of Aliphatic Bromides." Journal of the American Chemical Society 140, no. 50 (2018): 17433–38. http://dx.doi.org/10.1021/jacs.8b12025.

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32

Tollefson, Emily J., Lucas W. Erickson, and Elizabeth R. Jarvo. "Stereospecific Intramolecular Reductive Cross-Electrophile Coupling Reactions for Cyclopropane Synthesis." Journal of the American Chemical Society 137, no. 31 (2015): 9760–63. http://dx.doi.org/10.1021/jacs.5b03870.

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33

Duan, Jicheng, Ke Wang, Guang‐Li Xu, et al. "Cross‐Electrophile C(sp 2 )−Si Coupling of Vinyl Chlorosilanes." Angewandte Chemie International Edition 59, no. 51 (2020): 23083–88. http://dx.doi.org/10.1002/anie.202010737.

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34

Duan, Jicheng, Ke Wang, Guang‐Li Xu, et al. "Cross‐Electrophile C(sp 2 )−Si Coupling of Vinyl Chlorosilanes." Angewandte Chemie 132, no. 51 (2020): 23283–88. http://dx.doi.org/10.1002/ange.202010737.

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35

Everson, Daniel A., and Daniel J. Weix. "ChemInform Abstract: Cross-Electrophile Coupling: Principles of Reactivity and Selectivity." ChemInform 45, no. 31 (2014): no. http://dx.doi.org/10.1002/chin.201431261.

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36

Deng, Li-Fan, Yingwei Wang, Shiyang Xu, et al. "Palladium catalysis enables cross-coupling–like S N 2-glycosylation of phenols." Science 382, no. 6673 (2023): 928–35. http://dx.doi.org/10.1126/science.adk1111.

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Despite their importance in life and material sciences, the efficient construction of stereo-defined glycosides remains a challenge. Studies of carbohydrate functions would be advanced if glycosylation methods were as reliable and modular as palladium (Pd)-catalyzed cross-coupling. However, Pd-catalysis excels in forming sp 2 -hybridized carbon centers whereas glycosylation mostly builds sp 3 -hybridized C–O linkages. We report a glycosylation platform through Pd-catalyzed S N 2 displacement from phenols toward bench-stable, aryl-iodide–containing glycosyl sulfides. The key Pd(II) oxidative ad
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37

Wang, Zheng-Ying, Shi-Zheng Liu, Cong Guo та ін. "Nickel-catalyzed γ-alkylation of cyclopropyl ketones with unactivated primary alkyl chlorides: balancing reactivity and selectivity via halide exchange". RSC Advances 14, № 18 (2024): 12883–87. http://dx.doi.org/10.1039/d4ra02616k.

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Nickel-catalyzed cross-electrophile coupling of cyclopropyl ketones and alkyl chlorides. High reactivity and selectivity can be achieved with sodium iodide as a cocatalyst that generates a low concentration of alkyl iodide via halide exchange.
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38

Wu, Fan, Cheng Ye та Weiqi Tong. "Nickel-Catalyzed Reductive Cross-Coupling of Oxalates Derived from α-Hydroxy Carbonyls with Vinyl Bromides". Synthesis 54, № 09 (2022): 2251–57. http://dx.doi.org/10.1055/s-0040-1719881.

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AbstractA nickel-catalyzed cross-electrophile coupling is disclosed in which a range of vinyl bromides were utilized as electrophiles with oxalates derived from α-hydroxy carbonyls as precursors to carbonyl radical coupling partners. This method is compatible with a broad range of functional groups, providing a complementary solution for the construction of β,γ-unsaturated carbonyl compounds.
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39

Walczak, Maciej, Feng Zhu, and Tianyi Yang. "Glycosyl Stille Cross-Coupling with Anomeric Nucleophiles – A General Solution to a Long-Standing Problem of Stereocontrolled Synthesis of C-Glycosides." Synlett 28, no. 13 (2017): 1510–16. http://dx.doi.org/10.1055/s-0036-1589020.

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Aryl C-glycosides are common structural motifs found in bioactive natural products and commercially available drugs. Despite their importance, most chemical methods to prepare C-glycosides have relied on the nucleophilic addition/substitution of a glycosyl electrophile, which result in variable anomeric selectivities and yields. Furthermore, these methods are not compatible with saccharides containing free hydroxyl groups. Here, we describe a direct cross-coupling reaction of anomeric nucleophiles (anomeric stannanes) and aryl halides. This method is the first general approach to the synthesis
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40

Sumida, Yuto, Takamitsu Hosoya, and Tomoe Sumida. "Nickel-Catalyzed Reductive Cross-Coupling of Aryl Triflates and Nonaflates with Alkyl Iodides." Synthesis 49, no. 16 (2017): 3590–601. http://dx.doi.org/10.1055/s-0036-1588464.

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A nickel-catalyzed cross-electrophile coupling of aryl triflates and nonaflates with alkyl iodides using manganese(0) as a reductant is described. The method is applicable to the reductive alkylation of various aryl sulfonates, including o-borylaryl triflate, which enabled efficient construction of diverse alkylated arenes under mild conditions.
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41

Hansen, Eric C., Changfeng Li, Sihang Yang, Dylan Pedro, and Daniel J. Weix. "Coupling of Challenging Heteroaryl Halides with Alkyl Halides via Nickel-Catalyzed Cross-Electrophile Coupling." Journal of Organic Chemistry 82, no. 14 (2017): 7085–92. http://dx.doi.org/10.1021/acs.joc.7b01334.

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42

Lin, Quan, Guobin Ma, and Hegui Gong. "Ni-Catalyzed Formal Cross-Electrophile Coupling of Alcohols with Aryl Halides." ACS Catalysis 11, no. 22 (2021): 14102–9. http://dx.doi.org/10.1021/acscatal.1c04239.

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43

Wu, Ting-Feng, Yue-Jiao Zhang, Yue Fu, et al. "Zirconium-redox-shuttled cross-electrophile coupling of aromatic and heteroaromatic halides." Chem 7, no. 7 (2021): 1963–74. http://dx.doi.org/10.1016/j.chempr.2021.06.007.

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44

Hewitt, Kirsten A., Pei-Pei Xie, Taylor A. Thane, et al. "Nickel-Catalyzed Domino Cross-Electrophile Coupling Dicarbofunctionalization Reaction To Afford Vinylcyclopropanes." ACS Catalysis 11, no. 23 (2021): 14369–80. http://dx.doi.org/10.1021/acscatal.1c04235.

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45

Huihui, Kierra M. M., Jill A. Caputo, Zulema Melchor, et al. "Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides." Journal of the American Chemical Society 138, no. 15 (2016): 5016–19. http://dx.doi.org/10.1021/jacs.6b01533.

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46

Shimkin, Kirk W., and John Montgomery. "Synthesis of Tetrasubstituted Alkenes by Tandem Metallacycle Formation/Cross-Electrophile Coupling." Journal of the American Chemical Society 140, no. 23 (2018): 7074–78. http://dx.doi.org/10.1021/jacs.8b04637.

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47

McGeough, Catherine P., Alexandra E. Strom, and Timothy F. Jamison. "Ni-Catalyzed Cross-Electrophile Coupling for the Synthesis of Skipped Polyenes." Organic Letters 21, no. 10 (2019): 3606–9. http://dx.doi.org/10.1021/acs.orglett.9b01019.

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48

Weix, Daniel, Daniel Everson, and Joseph Buonomo. "Nickel-Catalyzed Cross-Electrophile Coupling of 2-Chloropyridines with Alkyl Bromides." Synlett 25, no. 02 (2013): 233–38. http://dx.doi.org/10.1055/s-0033-1340151.

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49

Huang, Huan-Ming. "Electrifying cross-electrophile coupling." Nature Synthesis, June 23, 2022. http://dx.doi.org/10.1038/s44160-022-00102-8.

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50

Jarvo, Elizabeth R., and Amberly B. Sanford. "Harnessing C–O Bonds in Stereoselective Cross-Coupling and Cross-Electrophile Coupling Reactions." Synlett, November 27, 2020. http://dx.doi.org/10.1055/s-0040-1705987.

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AbstractWe discuss our laboratory’s research in the activation of alcohol derivatives in cross-coupling and cross-electrophile coupling reactions. Our developed methods enable the use of secondary alcohols to afford tertiary stereogenic centers, which we applied to the synthesis of pharmaceutically relevant compounds and substructures. We first ­discuss the synthesis of bioactive compounds through stereospecific Kumada cross-coupling reactions and follow this with a discussion on the development of our stereoselective cross-electrophile coupling ­reaction to synthesize cyclopropanes.1 Introduc
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