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Reaction of B 2 ( o ‐tol) 4 with CO and Isocyanides: Cleavage of the C≡O Triple Bond and Direct C−H Borylations
Author(s) -
Katsuma Yuhei,
Tsukahara Nana,
Wu Linlin,
Lin Zhenyang,
Yamashita Makoto
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201800878
Subject(s) - diborane , chemistry , triple bond , cleavage (geology) , boranes , bond cleavage , oxygen atom , carbon atom , medicinal chemistry , atom (system on chip) , lewis acids and bases , stereochemistry , boron , catalysis , double bond , organic chemistry , molecule , ring (chemistry) , materials science , fracture (geology) , composite material , computer science , embedded system
The reaction of highly Lewis acidic tetra( o ‐tolyl)diborane(4) with CO afforded a mixture of boraindane and boroxine by the cleavage of the C≡O triple bond. 13 C labeling experiments confirmed that the carbon atom in the boraindane stems from CO. Simultaneously, formation of boroxine 3 could be considered as borylene transfer to capture the oxygen atom from CO. The reaction of diborane(4) with t Bu−NC afforded an azaallene, while the reaction with Xyl−NC furnished cyclic compounds by direct C−H borylations.