Transition-metal-catalyzed carbonylative cross-coupling with alkyl carbon nucleophiles

Transition-metal-catalyzed carbonylative reaction is an efficient approach to construct carbonyl-containing compounds with a high atomic economy in modern organic synthesis. This review focuses on the transition-metal-catalyzed carbonylation of aliphatic carbon nucleophiles. The carbonylation reactions with alkyl carbon nucleophiles, including alkyl boranes, tetraalkyltins, alkylzinc, trialkyl aluminium, alkylindium, and alkylzirconium reagents have been summarized and discussed here. Transition-metal-catalyzed carbonylative reaction is an efficient methodology for the synthesis of carbonyl-containing compounds with high atom economy and is widely applied in laboratory and industrial processes. However, due to their instability and excessive activity, alkyl carbon nucleophiles are less applied than alcohols, amines, or aryl carbon nucleophiles in carbonylation. In this review, we summarize and discuss carbonylative coupling reactions with alkyl boranes, tetraalkyl tins, alkyl zinc, trialkyl aluminium, alkyl indium, and alkyl zirconium reagents in past decades; we thus hope to increase the interest of researchers in related fields and promote further developments in this area. Carbonylative coupling reactions with alkyl carbon nucleophiles are summarized. Various studied alkyl carbon nucleophiles, including alkyl boranes, tetraalkyl tins, alkyl zinc, trialkyl aluminium, alkyl indium and alkyl zirconium reagents, are discussed here. With this review, we wish to attract more attention from researchers and further promote the developments in this topic.