Carbonylative Coupling Reactions with Organometallic Reagents

Beller and X.-F. Wu, Transition Metal Catalyzed Carbonylation Reactions, DOI 10.1007/978-3-642-39016-6 4, Springer-Verlag Berlin Heidelberg 2013 

4 Caibonylative Coupling Reactions with Organometallic Reagents 

Ishikura and Terashima described an application of the carbonylative coupling of organohalides or vinyl triflates in a one-pot procedure using indolylborates as a 

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In this chapter we have discussed the carbonylative transformation of C-X with organometallic reagents as coupling partners. Ketones were produced selectively. In the reaction mechanism, transmetalation is normally involved before reductive elimination. 

Coupling of organometallic reagents with hahdes in a carbon monoxide atmosphere leads to ketones by incorporation of a carbonylation step.147 148 These reactions involved a migration of one of the organic subsituents to the carbonyl carbon, followed by reductive elimination. These reactions can be carried out with stannanes149 or boronic acids150 151 as the nucleophilic component. 

Transition metal-catalyzed carbonylation reactions represent an enormous toolbox for CO-X bond formation (X = C, N, O, etc.). While most coupling reactions take place with heteronucleophiles nowadays, carbonylations including C-H activation are attracting more and more attention because the use of stoichiometric amounts of organometallic reagents can be avoided. 

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