Iridium-catalyzed B-H insertion of sulfoxonium ylides and borane adducts: a versatile platform to α-boryl carbonyls

Iridium-catalyzed boron-hydrogen bond insertion reactions of trimethylamine-borane and sulfoxonium ylides have been demonstrated, furnishing α-boryl ketones in moderate to excellent yields in most cases (51 examples; up to 84%). This practical and scalable insertion reaction showed broad substrate s...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-01, Vol.56 (3), p.423-426
Main Authors: Zhang, Shang-Shi, Xie, Hui, Shu, Bing, Che, Tong, Wang, Xiao-Tong, Peng, Dongming, Yang, Fan, Zhang, Luyong
Format: Article
Language:English
Subjects:
Adducts
Boron
Carbonyls
catalytic activity
chemical bonding
Chemical reactions
drugs
Hydrogen bonds
Insertion
Iridium
Ketones
Substrates
Trimethylamine
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Summary:Iridium-catalyzed boron-hydrogen bond insertion reactions of trimethylamine-borane and sulfoxonium ylides have been demonstrated, furnishing α-boryl ketones in moderate to excellent yields in most cases (51 examples; up to 84%). This practical and scalable insertion reaction showed broad substrate scope, high functional-group compatibility and could be applied in late-stage modification of structurally complex drug compounds. Further synthetic applications were also demonstrated. Iridium-catalyzed boron-hydrogen bond insertion reactions of trimethylamine-borane and sulfoxonium ylides have been demonstrated, furnishing α-boryl ketones in moderate to excellent yields in most cases (51 examples; up to 84%).
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/c9cc08795h