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. 2006 Feb 8;128(5):1446-7.
doi: 10.1021/ja057622a.

Anti-markovnikov N-H and O-H additions to electron-deficient olefins catalyzed by well-defined Cu(I) anilido, ethoxide, and phenoxide systems

Colleen Munro-Leighton  1 , Elizabeth D Blue, T Brent Gunnoe
Affiliations

Anti-markovnikov N-H and O-H additions to electron-deficient olefins catalyzed by well-defined Cu(I) anilido, ethoxide, and phenoxide systems

Colleen Munro-Leighton et al. J Am Chem Soc. .

Abstract

The monomeric Cu(I) complexes (IPr)Cu(Z) (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, Z = NHPh, OEt, or OPh) react with YH (Y = PhNH, PhCH2NH, EtO, or PhO) to catalytically add Y-H bonds across the C=C bond of electron-deficient olefins to yield anti-Markovnikov organic products. Catalytic activity has been observed for olefins CH2C(H)(X) with X = CN, C(O)Me, or CO2Me as well as crotononitrile. Preliminary studies implicate an intermediate in which the C-Y bond forms through a nucleophilic addition pathway.

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