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Azaborabutadienes: Synthesis by Metal‐Free Carboboration of Nitriles and Utility as Building Blocks for B,N‐Heterocycles
Author(s) -
Kong Lingbing,
Lu Wei,
Li Yongxin,
Ganguly Rakesh,
Kinjo Rei
Publication year - 2016
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.201608994
Subject(s) - regioselectivity , isomerization , chemistry , ring (chemistry) , block (permutation group theory) , reactivity (psychology) , combinatorial chemistry , boron , stereochemistry , medicinal chemistry , catalysis , organic chemistry , combinatorics , mathematics , medicine , alternative medicine , pathology
Metal‐free regioselective carboboration of arylnitriles with L 2 PhB: ( 1 : L=oxazol‐2‐ylidene) catalyzed by Et 3 B afforded the unprecedented acyclic 2‐aza‐4‐borabutadienes 2 , thus demonstrating a new strategy to construct a B,C,N‐mixed π‐system involving B=C and C=N bonds. Thermal isomerization of 2 gave C‐borylimines ( 3 ), and diverse reactivity of 2 a towards several substrates, such as H + , F + , O 2 , S, Se, and isonitriles, allowed construction of boron‐containing heterocycles with various ring sizes, thus illustrating the utility of 2 as a synthetic building block.