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Jia, Shikun; Xing, Dong; Zhang, Dan; Hu, Wenhao
Angewandte Chemie (International ed.), 11/2014, Volume: 53, Issue: 48Journal Article
Asymmetric functionalization of aromatic CH bonds of N,N-disubstituted anilines with diazo compounds and imines is reported for the efficient construction of alpha,alpha-diaryl benzylic quaternary stereocenters in good yields with high diastereoselectivities and excellent enantioselectivities. This RhII/chiral phosphoric acid cocatalyzed transformation is proposed to proceed through a metal-carbene-induced zwitterionic intermediate which undergoes electrophilic trapping. To the best of our knowledge, this is the first asymmetric example of metal carbene-induced intermolecular functionalization of aryl CH bonds.
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