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  • Lewis acid catalyzed direct cyanation of indoles and pyrroles with N-cyano-N-phenyl-p-toluenesulfonamide (NCTS).

Lewis acid catalyzed direct cyanation of indoles and pyrroles with N-cyano-N-phenyl-p-toluenesulfonamide (NCTS).

Organic letters (2011-09-16)
Yang Yang, Yan Zhang, Jianbo Wang
ABSTRACT

BF(3)·OEt(2)-catalyzed direct cyanation of indoles and pyrroles using a less toxic, bench-stable, and easily handled electrophilic cyanating agent N-cyano-N-phenyl-para-toluenesulfonamide (NCTS) affords 3-cyanoindoles and 2-cyanopyrroles in good yields with excellent regioselectivity. The substrate scope is broad with respect to indoles and pyrroles.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
p-Toluenesulfonamide, ReagentPlus®, ≥99%
Sigma-Aldrich
p-Toluenesulfonamide, reagent grade, 98%