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Copper-Catalyzed Triboration: Straightforward, Atom-Economical Synthesis of 1,1,1-Triborylalkanes from Terminal Alkynes and HBpin.

ABSTRACT: A convenient and efficient one-step synthesis of 1,1,1-triborylalkanes was achieved via sequential dehydrogenative borylation and double hydroborations of terminal alkynes with HBpin (HBpin=pinacolborane) catalyzed by inexpensive and readily available Cu(OAc)₂ . This process proceeds under mild conditions, furnishing 1,1,1-tris(boronates) with wide substrate scope, excellent selectivity, and good functional-group tolerance, and is applicable to gram-scale synthesis without loss of yield. The 1,1,1-triborylalkanes can be used in the preparation of ?-vinylboronates and borylated cyclic compounds, which are valuable but previously rare compounds. Different alkyl groups can be introduced stepwise via base-mediated deborylative alkylation to produce racemic tertiary alkyl boronates, which can be readily transformed into useful tertiary alcohols.

SUBMITTER: Liu X

PROVIDER: S-EPMC6972527 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Copper-Catalyzed Triboration: Straightforward, Atom-Economical Synthesis of 1,1,1-Triborylalkanes from Terminal Alkynes and HBpin.

Liu Xiaocui X Ming Wenbo W Zhang Yixiao Y Friedrich Alexandra A Marder Todd B TB

Angewandte Chemie (International ed. in English) 20191111 52

A convenient and efficient one-step synthesis of 1,1,1-triborylalkanes was achieved via sequential dehydrogenative borylation and double hydroborations of terminal alkynes with HBpin (HBpin=pinacolborane) catalyzed by inexpensive and readily available Cu(OAc)2 . This process proceeds under mild conditions, furnishing 1,1,1-tris(boronates) with wide substrate scope, excellent selectivity, and good functional-group tolerance, and is applicable to gram-scale synthesis without loss of yie ...[more]

PMID: 31490606

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