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C-Propargylation Overrides O-Propargylation in Reactions of Propargyl Chloride with Primary Alcohols: Rhodium-Catalyzed Transfer Hydrogenation.

ABSTRACT: The canonical SN 2 behavior displayed by alcohols and activated alkyl halides in basic media (O-alkylation) is superseded by a pathway leading to carbinol C-alkylation under the conditions of rhodium-catalyzed transfer hydrogenation. Racemic and asymmetric propargylations are described.

SUBMITTER: Liang T

PROVIDER: S-EPMC4965293 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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C-Propargylation Overrides O-Propargylation in Reactions of Propargyl Chloride with Primary Alcohols: Rhodium-Catalyzed Transfer Hydrogenation.

Liang Tao T Woo Sang Kook SK Krische Michael J MJ

Angewandte Chemie (International ed. in English) 20160620 32

The canonical SN 2 behavior displayed by alcohols and activated alkyl halides in basic media (O-alkylation) is superseded by a pathway leading to carbinol C-alkylation under the conditions of rhodium-catalyzed transfer hydrogenation. Racemic and asymmetric propargylations are described. ...[more]

PMID: 27321353

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