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Merck

Lewis acid catalyzed cascade reaction to carbazoles and naphthalenes via dehydrative [3 + 3]-annulation.

Organic letters (2014-06-25)
Shaoyin Wang, Zhuo Chai, Yun Wei, Xiancui Zhu, Shuangliu Zhou, Shaowu Wang
RÉSUMÉ

A novel Lewis acid catalyzed dehydrative [3 + 3]-annulation of readily available benzylic alcohols and propargylic alcohols was developed to give polysubstituted carbazoles and naphthalenes in moderate to good yields with water as the only byproduct. The reaction was presumed to proceed via a cascade process involving Friedel-Crafts-type allenylation, 1,5-hydride shift, 6π-eletrocyclization, and Wagner-Meerwein rearrangement.

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