Michael Krische Group – Professor Product Portal

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Professor Michael Krische

The Krische group has developed a broad class of “C-C bond forming transfer hydrogenations” wherein the exchange of hydrogen between alcohols and unsaturated reactants serves to generate aldehyde-organometal pairs that combine to give products of carbonyl addition. This methodology enables direct alcohol CH-functionalization, avoiding discrete alcohol-to-aldehyde redox manipulations. The indicated cyclometallated iridium C,O-benzoate complexes can be handled on the bench top and deployed in aqueous organic media.

Krische Group website
Link to Aldrichimica Acta review (2015) 

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Soo Bong Han et. al
Journal of the American Chemical Society, 132(26), 9153-9156 (2010)
Using the ortho-cyclometalated pi-allyl iridium precatalyst (R)-I derived from [Ir(cod)Cl](2), 4-cyano-3-nitrobenzoic acid, (R)-SEGPHOS, and allyl acetate, enantioselective transfer hydrogenation of alpha-(trimethylsilyl)allyl acetate in the presenc...Read More
Yong Jian Zhang et. al
Journal of the American Chemical Society, 132(13), 4562-4563 (2010)
Enantioselective transfer hydrogenation of carbonate 1a in the presence of aromatic, allylic, or aliphatic alcohols 2a-2i employing a cyclometalated iridium C,O-benzoate derived from allyl acetate, 4-cyano-3-nitrobenzoic acid and (S)-SEGPHOS deliver...Read More
Xin Gao et. al
Journal of the American Chemical Society, 133(32), 12795-12800 (2011)
Under the conditions of transfer hydrogenation employing the cyclometalated iridium catalyst (R)-I derived from [Ir(cod)Cl](2), allyl acetate, 4-cyano-3-nitrobenzoic acid, and the chiral phosphine ligand (R)-SEGPHOS, a-methylallyl acetate engages 1...Read More
Soo Bong Han et. al
Journal of the American Chemical Society, 132(6), 1760-1761 (2010)
Enantioselective transfer hydrogenation of gem-dibenzoate 1e in the presence of aromatic, alpha,beta-unsaturated, or aliphatic aldehydes 2a-i mediated by isopropyl alcohol and employing a cyclometalated iridium C,O-benzoate derived from allyl acetat...Read More
Soo Bong Han et. al
Journal of the American Chemical Society, 131(20), 6916-6917 (2009)
Enantioselective transfer hydrogenation of 1,1-dimethylallene 1a in the presence of aromatic, alpha,beta-unsaturated, or aliphatic aldehydes 2a-i mediated by 2-propanol and employing a cyclometalated iridium C,O-benzoate derived from allyl acetate,...Read More
Xin Gao et. al
Journal of Organic Chemistry, 76(7), 2350-2354 (2011)
The cyclometalated iridium complex (S)-I derived from [Ir(cod)Cl](2), 4-cyano-3-nitrobenzoic acid, allyl acetate, and (S)-SEGPHOS is conveniently isolated by precipitation or through conventional silica gel flash chromatography. This single-componen...Read More