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Ynones Merge Activation/Conjugate Addition of Chalcogenoborates ArE‐Bpin (E=Se, S)
Author(s) -
Civit Marc G.,
Sanz Xavier,
Vogels Christopher M.,
Bo Carles,
Westcott Stephen A.,
Fernández Elena
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500650
Subject(s) - chemistry , moiety , conjugate , alkyne , merge (version control) , stereochemistry , reagent , stereoselectivity , organic chemistry , catalysis , information retrieval , mathematical analysis , mathematics , computer science
The “pull–push” effect of the Bpin moiety in ArE‐Bpin reagents (E=Se, S) is demonstrated by the Lewis acid interaction with the carbonyl group of ynones and the concomitant delivery of ArSe or ArS to the electron‐deficient alkyne with impressive stereoselectivity. The two component reactivity is carried out in methanol to generate ( Z )‐β‐(arylseleno)‐α,β‐unsaturated ketones and ( Z )‐β‐(arylsulfuro)‐α,β‐unsaturated ketones with a consensus between experimental and theoretical understanding of the mechanism.