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Alkyne hydroacylation: switching regioselectivity by tandem ruthenium catalysis.

ABSTRACT: By using tandem Ru-catalysis, internal alkynes can be coupled with aldehydes for the synthesis of ?,?-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.

SUBMITTER: Chen QA

PROVIDER: S-EPMC4445957 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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Alkyne hydroacylation: switching regioselectivity by tandem ruthenium catalysis.

Chen Qing-An QA Cruz Faben A FA Dong Vy M VM

Journal of the American Chemical Society 20150121 9

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. ...[more]

PMID: 25608143

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