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Copper‐Catalyzed Triboration: Straightforward, Atom‐Economical Synthesis of 1,1,1‐Triborylalkanes from Terminal Alkynes and HBpin
Author(s) -
Liu Xiaocui,
Ming Wenbo,
Zhang Yixiao,
Friedrich Alexandra,
Marder Todd B.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201909376
Subject(s) - borylation , chemistry , alkyl , yield (engineering) , catalysis , substrate (aquarium) , alkylation , combinatorial chemistry , functional group , scope (computer science) , medicinal chemistry , organic chemistry , aryl , computer science , materials science , oceanography , polymer , metallurgy , geology , programming language
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 α‐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.