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Synthesis of Triborylalkenes from Terminal Alkynes by Iridium‐Catalyzed Tandem CH Borylation and Diboration
Author(s) -
Lee ChunI,
Shih WeiChun,
Zhou Jia,
Reibenspies Joseph H.,
Ozerov Oleg V.
Publication year - 2015
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.201507372
Subject(s) - borylation , hydroboration , iridium , alkyne , chemistry , catalysis , pincer movement , tandem , combinatorial chemistry , terminal (telecommunication) , ligand (biochemistry) , medicinal chemistry , organic chemistry , materials science , computer science , biochemistry , alkyl , receptor , aryl , composite material , telecommunications
Abstract A two‐step reaction to convert terminal alkynes into triborylalkenes is reported. In the first step, the terminal alkyne and pinacolborane (HBpin) are converted into an alkynylboronate, which is catalyzed by an iridium complex supported by a SiNN pincer ligand. In the second step, treatment of the reaction mixture with CO generates a new catalyst which mediates dehydrogenative diboration of alkynylboronate with pinacolborane. The mechanism of the diboration remains unclear but it does not proceed via intermediacy of hydroboration products or via B 2 pin 2 .