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Journal articles on the topic 'Wittig olefination'

Author: Grafiati

Published: 4 June 2025

Last updated: 1 August 2025

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1

Ilia, Gheorghe, Vasile Simulescu, Nicoleta Plesu, Vlad Chiriac, and Petru Merghes. "Wittig and Wittig–Horner Reactions under Sonication Conditions." Molecules 28, no. 4 (2023): 1958. http://dx.doi.org/10.3390/molecules28041958.

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Carbonyl olefinations are among the most important organic syntheses that form C=C bonds, as they usually have high yields and in addition offer excellent stereoselectivity. Due to these advantages, carbonyl olefinations have important pharmaceutical and industrial applications. These reactions contain an additional step of an α-functionalized carbanion to an aldehyde or ketone to produce alkenes, but syntheses performed using metal carbene complexes are also known. The Wittig reaction is an example of carbonyl olefination, one of the best ways to synthesize alkenes. This involves the chemical

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2

Khan, Ajmir, Mohammed G. Sarwar, and Sher Ali. "Reactivity and Stability of (Hetero)Benzylic Alkenes via the Wittig Olefination Reaction." Molecules 29, no. 2 (2024): 501. http://dx.doi.org/10.3390/molecules29020501.

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Wittig olefination at hetero-benzylic positions for electron-deficient and electron-rich heterocycles has been studied. The electronic effects of some commonly used protective groups associated with the N-heterocycles were also investigated for alkenes obtained in the context of the widely employed Wittig olefination reaction. It was observed that hetero-benzylic positions of the pyridine, thiophene and furan derivatives were stable after Wittig olefination. Similarly, electron-withdrawing groups (EWGs) attached to N-heterocycles (indole and pyrrole derivatives) directly enhanced the stability

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3

Lakhrissi, Mohammed, and Yves Chapleur. "Wittig Olefination of Lactones." Angewandte Chemie International Edition in English 35, no. 7 (1996): 750–52. http://dx.doi.org/10.1002/anie.199607501.

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4

Breit, Bernhard, and Stephan K. Zahn. "Domino hydroformylation–Wittig olefination–hydrogenation." Tetrahedron 61, no. 26 (2005): 6171–79. http://dx.doi.org/10.1016/j.tet.2005.03.112.

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5

Li, Qiang-Qiang, Zaher Shah, Jian-Ping Qu, and Yan-Biao Kang. "Direct Wittig Olefination of Alcohols." Journal of Organic Chemistry 83, no. 1 (2017): 296–302. http://dx.doi.org/10.1021/acs.joc.7b02720.

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6

Lum, Kenneth M., Vanessa J. Xavier, Michelle J. H. Ong, Charles W. Johannes, and Kok-Ping Chan. "Stabilized Wittig olefination for bioconjugation." Chemical Communications 49, no. 95 (2013): 11188. http://dx.doi.org/10.1039/c3cc45961f.

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7

Thiemann, Thies. "Solventless Wittig Olefination with Fluorinated Benzaldehydes." Journal of Chemical Research 2007, no. 6 (2007): 336–41. http://dx.doi.org/10.3184/030823407x225464.

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Fluorinated benzaldehydes undergo solventless Wittig olefination with stabilised phosphoranes. Even with less reactive, stabilised phosphoranes, such as acetylmethylidenetriphenylphosphorane, the reactions have been found to be exothermic.

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8

Pascariu, Aurelia, Gheorghe Ilia, Alina Bora, et al. "Wittig and Wittig-Horner reactions under phase transfer catalysis conditions." Open Chemistry 1, no. 4 (2003): 491–534. http://dx.doi.org/10.2478/bf02475230.

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AbstractWittig and Wittig-Horner reactions are favorite tools in preparative organic chemistry. These olefination methods enjoy widespread and recognition because of their simplicity, convenience, and effciency. Phase transfer catalysis (PTC) is a very important method in synthetic organic chemistry having many advantages over conventional, homogenous reaction procedures. In this paper, we attempt to summarize the aspects concerning Wittig and Wittig-Horner reactions that take place under phase transfer catalysis conditions.

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9

Watanabe, Masataka, Shuntaro Mataka, and Thies Thiemann. "One pot Sonogashira-coupling/Wittig olefination procedures." Journal of Chemical Research 2005, no. 10 (2005): 636–39. http://dx.doi.org/10.3184/030823405774663057.

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Bromoarylcarbaldehydes, bromoheteroarylcarbaldehydes, and bromoalkenals can be subjected to a one pot Sonogashira coupling–Wittig olefination reaction to give easy access to molecules with extended pi-systems.

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10

Dhumaskar, Kashinath L., Chinmay Bhat, and Santosh G. Tilve. "PDC-Mediated Tandem Oxidative–Wittig Olefination." Synthetic Communications 44, no. 10 (2014): 1501–6. http://dx.doi.org/10.1080/00397911.2013.862725.

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11

Wong, Gene W., and Clark R. Landis. "Iterative Asymmetric Hydroformylation/Wittig Olefination Sequence." Angewandte Chemie 125, no. 5 (2013): 1604–7. http://dx.doi.org/10.1002/ange.201208819.

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12

LAKHRISSI, M., and Y. CHAPLEUR. "ChemInform Abstract: Wittig Olefination of Lactones." ChemInform 27, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199628255.

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13

Wong, Gene W., and Clark R. Landis. "Iterative Asymmetric Hydroformylation/Wittig Olefination Sequence." Angewandte Chemie International Edition 52, no. 5 (2013): 1564–67. http://dx.doi.org/10.1002/anie.201208819.

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14

Yamamoto, Kyoko, Masataka Watanabe, Kyoko Ideta, Shuntaro Mataka, and Thies Thiemann. "Combined Suzuki Coupling – Wittig Olefination Reaction in Aqueous Medium." Zeitschrift für Naturforschung B 60, no. 12 (2005): 1299–307. http://dx.doi.org/10.1515/znb-2005-1215.

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15

Ramavath, Vijayalakshmi, Bapurao D. Rupanawar, Satish G. More, Ajay H. Bansode, and Gurunath Suryavanshi. "Hypervalent iodine(iii) induced oxidative olefination of benzylamines using Wittig reagents." New Journal of Chemistry 45, no. 19 (2021): 8806–13. http://dx.doi.org/10.1039/d1nj01170g.

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16

Miao, Pannan, Ruining Li, Xianfeng Lin, Liangming Rao, and Zhankui Sun. "Visible-light induced metal-free cascade Wittig/hydroalkylation reactions." Green Chemistry 23, no. 4 (2021): 1638–41. http://dx.doi.org/10.1039/d1gc00091h.

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Through a relay olefination and radical addition process, we developed cascade Wittig/hydroalkylation reactions induced by visible light. This metal-free radical approach features mild conditions, robustness, and excellent functionality tolerance.

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17

Hashim, Areej, Vijo Poulose, and Thies Thiemann. "3-(Biphenyl)acrylates by One-Pot Suzuki Cross Coupling–Wittig Olefination Reactions." Chemistry Proceedings 3, no. 1 (2020): 3. http://dx.doi.org/10.3390/ecsoc-24-08350.

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3-(Biphenyl)acrylates are prepared in good yield by one-pot Suzuki cross-coupling (Wittig olefination reactions). The central building blocks are 4-formyl- and 3-formylphenylboronic acids and the stabilized (carbomethoxymethylene)triphenylphosphorane. Examples of one-pot Suzuki–double Wittig combinations are also shown.

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18

Hashim, Areej, Vijo Poulose, and Thies Thiemann. "One Pot O-alkylation/Wittig Olefination of Hydroxybenzaldehydes in DMSO." Chemistry Proceedings 3, no. 1 (2020): 99. http://dx.doi.org/10.3390/ecsoc-24-08288.

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Hydroxybenzaldehydes are submitted to a one pot O-alkylation/Wittig olefination in dimethyl sulfoxide (DMSO) to give alkyl alkoxycinnamates. The reaction is carried out facilely and gives the products in high yield.

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19

Thiemann, Thies, Masataka Watanabe, Yasuko Tanaka, and Shuntaro Mataka. "One pot Suzuki coupling - Wittig olefination reactions." Journal of Chemical Research 2004, no. 11 (2004): 723–27. http://dx.doi.org/10.3184/0308234043431609.

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20

Reiter, Dominik, Philipp Frisch, Tibor Szilvási, and Shigeyoshi Inoue. "Heavier Carbonyl Olefination: The Sila-Wittig Reaction." Journal of the American Chemical Society 141, no. 42 (2019): 16991–96. http://dx.doi.org/10.1021/jacs.9b09379.

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21

Crimmin, Mark R., and Andrew J. P. White. "Wittig-olefination via an yttrium-coordinated betaine." Chemical Communications 48, no. 12 (2012): 1745. http://dx.doi.org/10.1039/c2cc16431k.

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22

Bera, Rabin, G. Dhananjaya, Shambu Nath Singh, Rajender Kumar, K. Mukkanti та Manojit Pal. "Microwave-accelerated Wittig olefination of β-chloroacroleins". Tetrahedron 65, № 7 (2009): 1300–1305. http://dx.doi.org/10.1016/j.tet.2008.12.036.

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23

Huang, Zheng-Zheng, Song Ye, Wei Xia, Yi-Hua Yu, and Yong Tang. "Wittig-Type Olefination Catalyzed by PEG-telluride." Journal of Organic Chemistry 67, no. 9 (2002): 3096–103. http://dx.doi.org/10.1021/jo025586h.

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24

Sabitha, Gowravaram, Sambit Nayak, M. Bhikshapathi, Maruthi Chittapragada, and J. Yadav. "Sequential One-Pot Isomerization-Wittig Olefination-Hydrogenation." Synthesis 2011, no. 22 (2011): 3661–68. http://dx.doi.org/10.1055/s-0030-1260232.

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25

Wang, Tongdao, Sonja Kohrt, Constantin G. Daniliuc, Gerald Kehr, and Gerhard Erker. "Borata-Wittig olefination reactions of ketones, carboxylic esters and amides with bis(pentafluorophenyl)borata-alkene reagents." Organic & Biomolecular Chemistry 15, no. 29 (2017): 6223–32. http://dx.doi.org/10.1039/c7ob01591g.

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26

Xu, Jin, Anqi Chen, Brendan Burkett, Qi Hua Ng, and Kok Ping Chan. "Synthesis of phosphine oxide based amphiphilic molecules via ring-opening Wittig olefination of a macrocyclic phosphoranylidene and their property study as non-ionic surfactants." RSC Advances 8, no. 36 (2018): 20406–10. http://dx.doi.org/10.1039/c8ra03324b.

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27

Bhosale, Viraj A., Dattatraya U. Ukale, and Suresh B. Waghmode. "Total synthesis of Sceletium alkaloids (±)-joubertinamine, (±)-epijoubertinamine, (±)-tortuosamine and formal synthesis of (±)-mesembrine, (±)-N-formyltortuosamine." New Journal of Chemistry 40, no. 11 (2016): 9432–40. http://dx.doi.org/10.1039/c6nj00630b.

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28

Kulkarni, Mukund G., Attrimuni P. Dhondge, Sanjay W. Chavhan, et al. "Total synthesis of (±)-coerulescine and (±)-horsfiline." Beilstein Journal of Organic Chemistry 6 (September 27, 2010): 876–79. http://dx.doi.org/10.3762/bjoc.6.103.

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29

Kulkarni, Mukund G., Dnyaneshwar D. Gaikwad, Ajit S. Borhade, et al. "Wittig Olefination–Claisen Rearrangement Protocol for Cyclohexene Annulation." Synthetic Communications 40, no. 3 (2010): 423–33. http://dx.doi.org/10.1080/00397910902985473.

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30

Sabitha, Gowravaram, M. Muralidhar Reddy, D. Srinivas, and J. S. Yadov. "Microwave irradiation: Wittig olefination of lactones and amides." Tetrahedron Letters 40, no. 1 (1999): 165–66. http://dx.doi.org/10.1016/s0040-4039(98)80048-8.

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31

Ishmuratov, G. Yu, V. A. Vydrina, I. S. Nazarov, et al. "Wittig Olefination of Menthone Lactol and Its Aluminate." Chemistry of Natural Compounds 48, no. 6 (2013): 981–84. http://dx.doi.org/10.1007/s10600-013-0444-0.

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32

Koreeda, Masato, Paresh D. Patel, and Lindsey Brown. "Z-Stereoselective Wittig olefination of 2-oxygenated cyclohexanones." Journal of Organic Chemistry 50, no. 26 (1985): 5910–12. http://dx.doi.org/10.1021/jo00350a108.

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33

Kayser, Margaret M., Krista L. Hatt, Heshui Yu, and Donald L. Hooper. "On the mechanism of Wittig reactions with cyclic anhydrides. II." Canadian Journal of Chemistry 71, no. 7 (1993): 1010–21. http://dx.doi.org/10.1139/v93-135.

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A study by NMR spectroscopic methods and trapping experiments of the mechanism of Wittig reactions between stabilized phosphoranes and unsymmetrically substituted cyclic anhydrides suggests that two reactions are involved: (1) a low-energy, reversible formation of acyclic adducts; and (2) a higher energy "Wittig olefination" reaction leading to enol-lactones. The latter, more selective, transformation requires a more highly organized transition state in which π-stacking and stabilizing complexations are important factors.

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34

Nikitin, Kirill, Anna C. Vetter, Helge Müller-Bunz, and Jimmy Muldoon. "Quaternary Phosphonium Carboxylates: Structure, Dynamics and Intriguing Olefination Mechanism." Synthesis 54, no. 07 (2021): 1745–52. http://dx.doi.org/10.1055/s-0037-1610788.

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AbstractWe have earlier shown how the Wittig chemistry can be done using novel Eigenbase phosphonium carboxylate reagents. Here we discuss the phenomenon of ion pairing, their solution tautomerism, solid-state structure, and mechanistic aspects of olefination. The results point to a complex process involving unfamiliar H-bond-driven ion-pair equilibria followed by standard Wittig reaction steps.

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35

Zhang, Kui, Lingchao Cai, Zhongyue Yang, K. N. Houk та Ohyun Kwon. "Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic γ-umpolung addition–Wittig olefination". Chemical Science 9, № 7 (2018): 1867–72. http://dx.doi.org/10.1039/c7sc04381c.

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36

Ronson, Thomas O., Martin H. H. Voelkel, Richard J. K. Taylor, and Ian J. S. Fairlamb. "Macrocyclic polyenynes: a stereoselective route to vinyl-ether-containing skipped diene systems." Chemical Communications 51, no. 38 (2015): 8034–36. http://dx.doi.org/10.1039/c5cc02091c.

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Novel macrocyclic polyenyne 1, with skipped unsaturation, has been constructed using Pd-catalysed cross-coupling, Wittig olefination and lithiation/alkylation methodologies; the final Stille macrocyclisation utilised the promising precatalyst, AsCat.

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37

Chavan, Subhash P., Prakash N. Chavan, and Lalit B. Khairnar. "A concise synthetic approach toward tamiflu (oseltamivir phosphate): cis-aziridine as the key synthon and RCM." RSC Adv. 4, no. 22 (2014): 11417–19. http://dx.doi.org/10.1039/c3ra47210h.

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The key synthon cis-aziridine has been efficiently utilised for the synthesis of tamiflu (oseltamivir phosphate), using Wittig olefination, Barbier addition, Mitsunobu reaction and ring closing metathesis (RCM) as key essentials.

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38

Marí, Frank, Paul M. Lahti, and William E. McEwen. "Molecular modeling of oxaphosphetane intermediates of wittig olefination reactions." Heteroatom Chemistry 1, no. 3 (1990): 255–59. http://dx.doi.org/10.1002/hc.520010311.

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39

Huang, Zheng-Zheng, Song Ye, Wei Xia, Yi-Hua Yu, and Yong Tang. "ChemInform Abstract: Wittig-Type Olefination Catalyzed by PEG-Telluride." ChemInform 33, no. 51 (2010): no. http://dx.doi.org/10.1002/chin.200251070.

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40

Henk, Thomas, Athanassios Giannis, and Konrad Sandhoff. "Wittig Olefination of Unprotected Carbohydrates with a Semistabilized Ylide." Liebigs Annalen der Chemie 1992, no. 2 (1992): 167–68. http://dx.doi.org/10.1002/jlac.199219920130.

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41

Crimmin, Mark R., and Andrew J. P. White. "ChemInform Abstract: Wittig Olefination via an Yttrium-Coordinated Betaine." ChemInform 43, no. 22 (2012): no. http://dx.doi.org/10.1002/chin.201222080.

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42

McNulty, James, and David McLeod. "Amine- and Sulfonamide-Promoted Wittig Olefination Reactions in Water." Chemistry - A European Journal 17, no. 32 (2011): 8794–98. http://dx.doi.org/10.1002/chem.201101153.

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43

Sabitha, Gowravaram, Sambit Nayak, M. Bhikshapathi, Maruthi Chittapragada, and J. S. Yadav. "ChemInform Abstract: Sequential One-Pot Isomerization-Wittig Olefination-Hydrogenation." ChemInform 43, no. 10 (2012): no. http://dx.doi.org/10.1002/chin.201210037.

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44

Srivastava, Vivek. "Active Ruthenium (0) Nanoparticles Catalyzed Wittig-Type Olefination Reaction." Catalysis Letters 147, no. 3 (2017): 693–703. http://dx.doi.org/10.1007/s10562-016-1943-y.

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45

Rommel, Susanne, Christian Belger, Jeanne-Marie Begouin, and Bernd Plietker. "Dual [Fe+Phosphine] Catalysis: Application in Catalytic Wittig Olefination." ChemCatChem 7, no. 8 (2015): 1292–301. http://dx.doi.org/10.1002/cctc.201500053.

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46

Shing, Tony K. M., Anthony W. H. Wong, Huiyan Li, Z. F. Liu, and Paul K. S. Chan. "Conformationally locked bicyclo[4.3.0]nonane carbanucleosides: synthesis and bio-evaluation." Org. Biomol. Chem. 12, no. 46 (2014): 9439–45. http://dx.doi.org/10.1039/c4ob01763c.

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d-Ribose was converted into 3 novel carbobicyclic nucleosides bearing a bicyclo[4.3.0]nonane framework in 16–19 steps with 5–12% overall yields involving a Wittig olefination and an intramolecular Diels–Alder reaction as the key steps.

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47

Sharada, Ambati, Lakshmi Srinivasa Rao Kundeti, Kallaganti V. S. Ramakrishna, and Kommu Nagaiah. "First Stereoselective Total Synthesis of Ciryneol C." SynOpen 03, no. 02 (2019): 59–66. http://dx.doi.org/10.1055/s-0037-1611876.

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The acetylene derivative Ciryneol C was isolated from the roots of C. japonicum. The asymmetric total synthesis of Ciryneol C was achieved in seven steps, with Horner–Wittig olefination, regioselective epoxide opening, and Cadiot–Chodkiewicz coupling reactions being the key steps.

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48

Korshin, Edward E., Gregory M. Leitus та Michael Bendikov. "Convenient access to readily soluble symmetrical dialkyl-substituted α-oligofurans". Org. Biomol. Chem. 12, № 34 (2014): 6661–71. http://dx.doi.org/10.1039/c4ob00898g.

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A combination of heteroatom directed lithiation/CuCl<sub>2</sub>-induced homocoupling, Wittig olefination/Pd-catalyzed transfer hydrogenation followed by Suzuki–Miyaura or Stille cross-coupling enables convenient access to dialkyl-substituted α-oligofurans of potential interest for organic electronics.

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49

Coldham, Iain, Alan J. Collis, Roger J. Mould, and Richard E. Rathmell. "Synthesis of 4-phenylpiperidines by tandem Wittig olefination–aza-Wittig rearrangement of 2-benzoylaziridines." J. Chem. Soc., Perkin Trans. 1, no. 21 (1995): 2739–45. http://dx.doi.org/10.1039/p19950002739.

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50

M, Heravi; Majid, V. Zadsirjan, H. Hamidi, M. Daraie, and T. Momeni. "Recent applications of the Wittig reaction in alkaloid synthesis." Alkaloids: Chemistry and Biology 84 (March 25, 2020): 201–334. https://doi.org/10.1016/bs.alkal.2020.02.002.

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The Wittig reaction is the chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide (the Wittig reagent) to afford an alkene and triphenylphosphine oxide. Noteworthy, this reaction results in the synthesis of alkenes in a selective and predictable fashion. Thus, it became as one of the keystone of synthetic organic chemistry, especially in the total synthesis of natural products, where the selectivity of a reaction is paramount of importance. A literature survey disclosed the existence of vast numbers of related reports and comprehensive reviews on the applications of this

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