Synthesis of 2-Substituted Propenes by Bidentate Phosphine-Assisted Methylenation of Acyl Fluorides and Acyl Chlorides with AlMe                         
                        3

Xiu Wang; Zhenhua Wang; Yuya Asanuma; Yasushi Nishihara

doi:10.1021/acs.orglett.9b01059

Synthesis of 2-Substituted Propenes by Bidentate Phosphine-Assisted Methylenation of Acyl Fluorides and Acyl Chlorides with AlMe ₃

Xiu Wang, Zhenhua Wang, Yuya Asanuma, Yasushi Nishihara

Research Institute for Interdisciplinary Science

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

Bidentate phosphine-assisted methylenation of acyl fluorides and acyl chlorides with substituted with aryl, alkenyl, and alkyl groups trimethylaluminum afforded an array of 2-substituted propene derivatives. The addition of a catalytic amount of DPPM increased an efficiency of the reactions. Trimethylaluminum as the methylenation reagent not only eliminates the presynthesis of methylene transfer reagent, but provides an efficient method for the synthesis of a series of 2-substituted propenes.

Original language	English
Pages (from-to)	3640-3643
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.9b01059
Publication status	Published - May 17 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Wang, X., Wang, Z., Asanuma, Y., & Nishihara, Y. (2019). Synthesis of 2-Substituted Propenes by Bidentate Phosphine-Assisted Methylenation of Acyl Fluorides and Acyl Chlorides with AlMe ₃ Organic Letters, 21(10), 3640-3643. https://doi.org/10.1021/acs.orglett.9b01059

Synthesis of 2-Substituted Propenes by Bidentate Phosphine-Assisted Methylenation of Acyl Fluorides and Acyl Chlorides with AlMe ₃ . / Wang, Xiu; Wang, Zhenhua; Asanuma, Yuya et al.
In: Organic Letters, Vol. 21, No. 10, 17.05.2019, p. 3640-3643.

Research output: Contribution to journal › Article › peer-review

Wang, X, Wang, Z, Asanuma, Y & Nishihara, Y 2019, ' Synthesis of 2-Substituted Propenes by Bidentate Phosphine-Assisted Methylenation of Acyl Fluorides and Acyl Chlorides with AlMe ₃ ', Organic Letters, vol. 21, no. 10, pp. 3640-3643. https://doi.org/10.1021/acs.orglett.9b01059

Wang X, Wang Z, Asanuma Y, Nishihara Y. Synthesis of 2-Substituted Propenes by Bidentate Phosphine-Assisted Methylenation of Acyl Fluorides and Acyl Chlorides with AlMe ₃ Organic Letters. 2019 May 17;21(10):3640-3643. doi: 10.1021/acs.orglett.9b01059

Wang, Xiu ; Wang, Zhenhua ; Asanuma, Yuya et al. / Synthesis of 2-Substituted Propenes by Bidentate Phosphine-Assisted Methylenation of Acyl Fluorides and Acyl Chlorides with AlMe ₃ In: Organic Letters. 2019 ; Vol. 21, No. 10. pp. 3640-3643.

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Synthesis of 2-Substituted Propenes by Bidentate Phosphine-Assisted Methylenation of Acyl Fluorides and Acyl Chlorides with AlMe ₃

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