Synthesis of cyclic amine boranes through triazole-gold(I)-catalyzed alkyne hydroboration.
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.
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA).
Qiaoyi
Q
Wang
Stephen E
SE
Motika
Novruz G
NG
Akhmedov
Jeffrey L
JL
Petersen
Xiaodong
X
Shi
alkynes; boranes; cyclization; gold; synthetic methods