Reaction of B-2(o-tol)(4) with CO and Isocyanides: Cleavage of the C O Triple Bond and Direct C-H Borylations

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. C-13 labeling experiments confirmed that the carbon atom in the boraindane stems from CO. Simultaneously, formation of boroxine 3 could be cons...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 57; no. 21; pp. 6109 - 6114
Main Authors Katsuma, Yuhei, Tsukahara, Nana, Wu, Linlin, Lin, Zhenyang, Yamashita, Makoto
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 22.05.2018
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
triple bonds
IRIDIUM-CATALYZED BORYLATION
ORGANOBORON COMPOUNDS
ORGANODIBORANE COMPOUNDS
bond cleavage
carbon monoxide
diborane
UNSYMMETRICAL DIBORANE
isocyanide
BORON-COMPOUNDS
MULTICOMPONENT REACTIONS
CARBON-MONOXIDE
DIBORON TETRACHLORIDE
TERT-BUTYLAZADIBORIRIDINE
LEWIS PAIR TEMPLATES
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Summary: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. C-13 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 Bu-t-NC afforded an azaallene, while the reaction with Xyl-NC furnished cyclic compounds by direct C-H borylations.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201800878