Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 10, Pages 1927-1946Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202000279
Keywords
acylsilanes; organosilicon compounds; photochemistry; siloxy carbenes; singlet nucleophilic carbenes
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Funding
- Australian Research Council [DE200100949]
- Australian Research Council [DE200100949] Funding Source: Australian Research Council
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Over fifty years ago, the 1,2-rearrangement of acylsilanes was first described by Adrian Brook and co-workers. This rearrangement (now termed the Brook rearrangement) yields reactive silicon-based singlet nucleophilic carbene (SNC) intermediates that participate in a variety of chemical transformations including 1,2-carbonyl addition, 1,4-addition to electron-deficient unsaturated bonds and insertion into C-H and O-H bonds. This review aims to cover the historical literature and recent advances with regard to these valuable silicon-based reagents and highlight additional aspects related to the intriguing reactivity of both the carbene and oxocarbenium intermediates.
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