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. 2020 Jul 7;11(30):7921-7926.
doi: 10.1039/d0sc02559c.

Reductive radical-initiated 1,2-C migration assisted by an azidyl group

Xueying Zhang  1 , Zhansong Zhang  1 , Jin-Na Song  2 , Zikun Wang  1
Affiliations

Reductive radical-initiated 1,2-C migration assisted by an azidyl group

Xueying Zhang et al. Chem Sci. .

Abstract

We report here a novel reductive radical-polar crossover reaction that is a reductive radical-initiated 1,2-C migration of 2-azido allyl alcohols enabled by an azidyl group. The reaction tolerates diverse migrating groups, such as alkyl, alkenyl, and aryl groups, allowing access to n+1 ring expansion of small to large rings. The possibility of directly using propargyl alcohols in one-pot is also described. Mechanistic studies indicated that an azidyl group is a good leaving group and provides a driving force for the 1,2-C migration.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. (A) Reductive radical-polar crossover reactions; (B) this work: reductive radical-initiated 1,2-C migration assisted by an azidyl group.
Scheme 1
Scheme 1. Mechanistic investigations.
Fig. 2
Fig. 2. Proposed mechanism.
See this image and copyright information in PMC

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