Title

Diastereoselective Oxidative C-N/C-O and C-N/C-N Bond Formation Tandems Initiated by Visible Light: Synthesis of Fused N‐Arylindolines

Document Type

Article

Publication Date

2015

Keywords

Cations, C-N bond formation, C-O bond formation, Fused-ring systems, Heterocycles, Photocatalysis

Abstract

The synthesis of fused N‐arylindolines using visible light photoredox catalysis has been developed. We previously described that photogenerated amine radical cations generate substituted indoles through an intermediate benzylic carbocation. Herein, we expand the application of this chemistry by trapping the benzylic carbocation with tethered heteronucleophiles. The reactivity of the photogenerated benzylic carbocation is explored and applied to a range of substrates with various electronic characters and ring constraints. The method described provides C‐2 and C‐3 fused indolines bearing a tetrasubstituted carbon stereocenter with greater than 99:1 diastereoselectivity in moderate to good yields.

Comments

Principal Investigator: Nan Zheng

Acknowledgements: This publication was supported by the University of Arkansas, Arkansas Bioscience Institute, Grant Number P30 GM103450 from the National Institute of General Medical Sciences of the National Institutes of Health (NIH), NSF Career Award under Award Number CHE‐1255539.

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