Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 52, Pages 18923-18927Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201909376
Keywords
boronic acid; cross-coupling; dehydrogenative borylation; gem-bisboronates; hydroboration
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Funding
- Julius-Maximilians-Universitt Wrzburg
- China Scholarship Council
- SUSTech
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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 alpha-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.
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