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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 23
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ARTICLES

Palladium-catalyzed cross-coupling of benzylzinc reagents with 2-bromo-3,3,3-trifluoropropene

An-Jun WangKey Laboratory of Biocatalysis and Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, ChinaView further author information
,
Yue-Guang LouKey Laboratory of Biocatalysis and Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, ChinaView further author information
,
Liang ZhaoKey Laboratory of Biocatalysis and Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, ChinaView further author information
,
Fei-Hu GouKey Laboratory of Biocatalysis and Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, ChinaView further author information
,
Lian WangKey Laboratory of Biocatalysis and Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, ChinaView further author information
,
Yanbo YuKey Laboratory of Biocatalysis and Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, ChinaView further author information
,
Jiwei GuKey Laboratory of Biocatalysis and Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, ChinaORCID Iconhttp://orcid.org/0000-0002-4908-7544View further author information
ORCID Icon &
Chun-Yang HeKey Laboratory of Biocatalysis and Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, ChinaCorrespondence[email protected]
ORCID Iconhttp://orcid.org/0000-0002-0599-7335View further author information
ORCID Icon show all
Pages 3329-3334 | Received 15 Aug 2019, Published online: 20 Sep 2019
 
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Abstract

α-Trifluoromethyl alkenes can be used as peptide isosteres, moreover, the pre-installed vinyl group make it possible that transformation to diverse fluorine-containing unities. However, the cross-coupling of benzyl group with α-trifluoromethyl alkenes has yet to be developed. In this report, we describe a general method for the cross-coupling of benzylzinc reagents with 2-bromo-3,3,3-trifluoropropene (BTP) to afford diverse α-trifluoromethylalkene derivatives by using Pd(TFA)2 as catalyst. This method takes advantage of cheap industrial available fluorine building blocks and easily prepared benzylzinc reagents to generate α-trifluoromethylalkene derivatives, which features with mild reaction conditions, wide substrate scope and feasibility of product transformations.

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Additional information

Funding

The National Natural Science Foundation of China [No. 81760624, 21702241, 21762053], Young Elite Scientists Sponsorship Program by Cast of the China Association for Science and Technology [No. 2015-41], the Programs of Guizhou Province [No. 2017-1225, 2018-1427] are warmly acknowledged for funding this work.

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