Abstract
Organogallium and ‐indium compounds are useful reagents in organic synthesis because of their moderate stability, efficient reactivity and high chemoselectivity. Carbogallation and ‐indation of a carbon‐carbon multiple bond achieves the simultaneous formation of carbon‐carbon and carbon‐metal bonds. Heterogallation and ‐indation construct carbon‐heteroatom and carbon‐metal bonds. Therefore, these reaction systems represent a significant synthetic method for organogalliums and ‐indiums. Many chemists have attempted to apply various types of unsaturated compounds such as alkynes, alkenes, and allenes to these reaction systems. This minireview provides an overview of carboindation and ‐gallation as well as heteroindation and ‐gallation.
Highlights
Introduction cases, organogalliums and indium species are generated as transient intermediates, but are not afforded as final products
Carbometalation of a carbon-carbon multiple-bond is an important and powerful method for the synthesis of organometallic compounds because organometallics are produced by the formation of a new carbon-carbon bond.[1]
Moderate reactivity of organogalliums and -indiums enables chemoselective reactions, and the organometallics produced by carbometalation are applicable to sequential reactions.[1,3]
Summary
Treatment of alkynyltrimethylsilane with GaCl3 in the presence of a catalytic amount of pyridine 2 gave dimeric product 4 after a workup with D2O, and two deuterium atoms were introduced at an exo-methylene moiety of 4, which suggested the possibility of a generation of 3 via carbogallation (Scheme 1a). Allylgallium species generated by transmetalation between allylsilane 9 and GaCl3 underwent syn-carbogallation (13) of alkynylsilane 1 (Scheme 2).[5]. Carbogallation using silyl enol ether 25, which is derived from a six-membered cyclic ketone, predominantly provided ethenylated cyclic ketone 26 with a equatorial vinyl group (Scheme 5).[10]. After returning to Osaka University he was promoted to Associate Professor in and full Professor in 2014 He is currently interested in organic synthesis using main group metals, and in the development of new types of Lewis acids with a designed organic framework. He is investigating reactive metal species that contribute to stereoselective carbon-carbon bond formation and their characterization based on spectroscopy and X-ray crystallographic analysis. Plausible reaction mechanism for carbogallation using silyl enolates and GaCl3
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