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Adv Synth Catal. 2015 Jul 6;357(10):2311-2316. Epub 2015 Jul 14.

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

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1
Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, Arkansas 72701, United States.

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 C2 and C3 fused indolines bearing a tetrasubstituted carbon stereocenter with greater than 99:1 diastereoselectivity in moderate to good yields.

KEYWORDS:

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

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