Strain-driven transition metal-free N-insertion for heterocycle synthesis Alexander Sandvoß and Johannes Wahl Johannes Gutenberg-Universität Mainz, Germany A method for the transition metal-free N -insertion into strained molecules was presented. O -Mesitylsulfonylhydroxylamine (MSH) was used as an amphiphilic reagent for the substitution of cyclic alcohols which could then undergo skeletal rearrangement to yield N -heterocyles. A variety of electronically differing pyrrolidines and benzannulated medium-sized rings in high yields (up to 92%) and excellent regioselectivity (>99:1) was prepared. The developed method was applied in a photochemical built-and-release strategy to yield indoles from commercial starting material over two steps.
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