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Silicon‐Derived Singlet Nucleophilic Carbene Reagents in Organic Synthesis
Author(s) -
Priebbenow Daniel L.
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000279
Subject(s) - carbene , chemistry , nucleophile , singlet state , reagent , reactivity (psychology) , photochemistry , reactive intermediate , combinatorial chemistry , organic chemistry , catalysis , excited state , medicine , physics , alternative medicine , pathology , nuclear physics
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.