Alkyne Hydroacylation: Switching Regioselectivity by Tandem Ruthenium Catalysis

By using tandem Ru-catalysis, internal alkynes can be coupled with aldehydes for the synthesis of β,γ-unsaturated ketones. The catalyst promotes alkyne transformations with high regioselectivity, with examples that include the differentiation of a methyl vs ethyl substituent on the alkyne. Mechanist...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-03, Vol.137 (9), p.3157-3160
Main Authors: Chen, Qing-An, Cruz, Faben A, Dong, Vy M
Format: Article
Language:English
Subjects:
Acylation
aldehydes
alkynes
Alkynes - chemistry
allene
Benzaldehydes - chemistry
Catalysis
catalysts
catalytic activity
ketones
ruthenium
Ruthenium - chemistry
Stereoisomerism
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Summary:By using tandem Ru-catalysis, internal alkynes can be coupled with aldehydes for the synthesis of β,γ-unsaturated ketones. The catalyst promotes alkyne transformations with high regioselectivity, with examples that include the differentiation of a methyl vs ethyl substituent on the alkyne. Mechanistic studies suggest that the regioselectivity results from a selective allene formation that is governed by allylic strain.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja512015w