trans-Hydroalkynylation of Internal 1,3-Enynes Enabled by Cooperative Catalysis

A cooperative catalyst system involving a Pd(0)/Senphos complex, tris(pentafluorophenyl)borane, copper bromide, and an amine base, is demonstrated to catalyze trans-hydroalkynylation of internal 1,3-enynes. For the first time, a Lewis acid catalyst is shown to promote the reaction involving the em...

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Bibliographic Details
Published in:	Journal of the American Chemical Society Vol. 145; no. 10; pp. 5624 - 5630
Main Authors:	Wang, Ziyong, Zhang, Chen, Wu, Jason, Li, Bo, Chrostowska, Anna, Karamanis, Panaghiotis, Liu, Shih-Yuan
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 15-03-2023
Subjects:	Chemical Sciences or physical chemistry Theoretical and
Online Access:	Get full text
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Summary:	A cooperative catalyst system involving a Pd(0)/Senphos complex, tris(pentafluorophenyl)borane, copper bromide, and an amine base, is demonstrated to catalyze trans-hydroalkynylation of internal 1,3-enynes. For the first time, a Lewis acid catalyst is shown to promote the reaction involving the emerging outer-sphere oxidative reaction step. The resulting cross-conjugated dieneynes are versatile synthons for organic synthesis, and their characterization reveals distinct photophysical properties depending on the positioning of the donor/acceptor substituents along the conjugation path.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0002-7863 1520-5126
DOI:	10.1021/jacs.3c00514