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【Mengchun Ye Group】Iron-Catalyzed Regioselective Transfer Hydrogenative Couplings of Unactivated Aldehydes with Simple Alkenes

Source:SKLEOC   Date:2016/10/12


   


The catalytic hydrogenative or transfer hydrogenative coupling of π-unsaturated reactants with carbonyl compounds has recently emerged as one of the most attractive C−C bond-forming methods.Unlike traditional catalytic reductive C−C couplings that employ alkyl metal reagents,metal hydrides,or elemental metals as the reducing agents, (transfer) hydrogenative couplings using hydrogen gas or hydrogen donors as greener terminal reductants provide a much less expensive and more environmentally benign C−C bond-forming process without generating stoichiometric amounts of metallic wastes.

Prof. Mengchun Ye has successfully developed an iron-catalyzed regioselective transfer hydrogenative coupling of aldehydes with alkenes using iPrOH as the hydrogen source under mild conditions. This new C−C bond-formation method enables the coupling of unactivated aldehydes, such as alkyl and aryl aldehydes, with simple alkenes, such styrene derivatives and branched α-olefins, for the first time and is based on the use of catalytic amounts of FeBr3. Preliminary mechanistic studies suggest that the reaction could proceed through a Prins/hydride-transfer pathway.

Link: http://onlinelibrary.wiley.com/doi/10.1002/anie.201602130/full