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Synthesis of Cyclic Amine Boranes through Triazole‐Gold(I)‐Catalyzed Alkyne Hydroboration
Author(s) -
Wang Qiaoyi,
Motika Stephen E.,
Akhmedov Novruz G.,
Petersen Jeffrey L.,
Shi Xiaodong
Publication year - 2014
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.201402614
Subject(s) - hydroboration , alkyne , boranes , chemistry , amine gas treating , catalysis , organic chemistry , triazole , combinatorial chemistry , boron
The first catalytic alkyne hydroboration of propargyl amine boranecarbonitriles is accomplished with triazole‐Au I complexes. While the typical [L‐Au] + species decomposes within minutes upon addition of amine boranecarbonitriles, the triazole‐modified gold catalysts (TA‐Au) remained active, and allowed the synthesis of 1,2‐BN‐cyclopentenes in one step with good to excellent yields. With good substrate tolerability and mild reaction conditions (open‐flask), this new method provides an alternative route to reach the interesting cyclic amine borane with high efficiency.