Generation and reactions of 3-lithio-1-(phenylsulfonyl) indole

MG Saulnier, GW Gribble

Index: Saulnier, Mark G.; Gribble, Gordon W. Journal of Organic Chemistry, 1982 , vol. 47, # 5 p. 757 - 761

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Citation Number: 192

Abstract

Treatment of l-(phenylsulfonyl)-3-iodoindole (6) with 2 equiv of tert-butyllithium (-100 OC THF) generates essentially quantitatively 3-lithio-l-(phenylsulfonyl) indole (1). Quenching 1 with various electrophiles gives 3-substituted indoles in good yield. Upon warming to room temperature, 1 cleanly rearranges to the more stable 2-lithio-l-(phenylsulfonyl) indole (2). An alternative procedure for the generation of 2 from 1-(phenylsulfony1) indole (8) with ...