Combined transition-metal- and organocatalysis: an atom economic C3 homologation of alkenes to carbonyl and carboxylic compounds

Chemistry : a European Journal
Susanne T KemmeBernhard Breit

Abstract

A combination of regioselective room-temperature/ambient-pressure hydroformylation (transition-metal catalysis) and decarboxylative Knoevenagel reactions (organocatalysis) allowed for the development of an efficient, one-pot C3 homologation of terminal alkenes to (E)-alpha,beta-unsaturated acids and esters, (E)-beta,gamma-unsaturated acids, (E)-alpha-cyano acrylic acids, and alpha,beta-unsaturated nitriles. All reactions proceed under mild conditions, tolerate a variety of functional groups, and furnish unsaturated carbonyl compounds in good yields and with excellent regio- and stereocontrol. Further, an iterative C2 homologation of (E)-alpha,beta-unsaturated carboxylic acids is possible through a combination of decarboxylative hydroformylation employing a supramolecular catalyst followed by decarboxylative Knoevenagel condensation with an organocatalyst.

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Citations

Feb 26, 2015·Chemical Communications : Chem Comm·Kaiwu DongMatthias Beller
Mar 30, 2012·Chemical Society Reviews·Petr Stěpnička
Jul 28, 2015·Angewandte Chemie·Haoquan LiMatthias Beller
Jun 20, 2015·Acta Crystallographica. Section E, Crystallographic Communications·Marcel SonneckSebastian Wohlrab
Mar 9, 2013·Angewandte Chemie·Baoguo ZhaoKuiling Ding
Jun 30, 2012·Chemistry : a European Journal·Julian StillerMathias Christmann

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