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Issue 10, 2020
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Double allylic defluorinative alkylation of 1,1-bisnucleophiles with (trifluoromethyl)alkenes: construction of all-carbon quaternary centers

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Abstract

A double allylic defluorinative alkylation reaction of 1,1-bisnucleophiles with (trifluoromethyl)alkenes is reported that occurs via the exclusively regioselective SN2 reaction. Various aliphatic nitriles, esters, and indolin-2-one derivatives could serve as 1,1-bisnucleophiles, delivering diverse attractive symmetric gem-difluoroalkene substituted products in high yields via the construction of all-carbon quaternary centers. Interestingly, the chemoselective SNV reaction between gem-difluoroalkenes and nucleophiles is completely inhibited. The nitrile group might help to stabilize the α-carbanion intermediates.

Graphical abstract: Double allylic defluorinative alkylation of 1,1-bisnucleophiles with (trifluoromethyl)alkenes: construction of all-carbon quaternary centers

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Article information


Submitted
23 Jan 2020
Accepted
05 Apr 2020
First published
09 Apr 2020

Org. Chem. Front., 2020,7, 1260-1265
Article type
Research Article

Double allylic defluorinative alkylation of 1,1-bisnucleophiles with (trifluoromethyl)alkenes: construction of all-carbon quaternary centers

Y. Cai, H. Zeng, C. Zhu, C. Liu, G. Liu and H. Jiang, Org. Chem. Front., 2020, 7, 1260
DOI: 10.1039/D0QO00121J

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