Photocatalytic Aerobic Double Friedel‐Crafts Reaction of Glycine Derivatives with Anilines: An Efficient Synthesis of Diarylmethanes

A mild and efficient aerobic double Friedel‐Crafts reaction of glycine derivatives with anilines has been developed with the assist of a photocatalytic system involving inexpensive Eosin Y as a photocatalyst. Under the optimized conditions, a range of N‐arylglycine derivatives underwent this oxidati...

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Veröffentlicht in:Asian journal of organic chemistry 2019-11, Vol.8 (11), p.2058-2064
Hauptverfasser: Sun, Bin, Yang, Jin, Zhang, Liang, Shi, Rongcheng, Zhang, Xun, Xu, Tengwei, Zhuang, Xiaohui, Zhu, Rui, Yu, Chuanming, Jin, Can
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Sprache:eng
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Zusammenfassung:A mild and efficient aerobic double Friedel‐Crafts reaction of glycine derivatives with anilines has been developed with the assist of a photocatalytic system involving inexpensive Eosin Y as a photocatalyst. Under the optimized conditions, a range of N‐arylglycine derivatives underwent this oxidative coupling reaction smoothly to give the desired diarylmethane derivatives with high para‐regioselectivities in moderate to excellent yields. Moreover, mechanistic studies revealed that this transformation followed a radical‐mediated pathway. This strategy featured mild conditions, operational simplicity, wide substrate scope and good functional group tolerance. A photocatalytic system, promoted by visible light, has been developed for a mild and efficient aerobic double Friedel‐Crafts alkylation of glycine derivatives with anilines.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201900542