- Lewis acid catalyzed cascade reaction to carbazoles and naphthalenes via dehydrative [3 + 3]-annulation.
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
PMID24960210
ABSTRACT
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.
MATERIALS
Product Number
Brand
Product Description
Sigma-Aldrich
Benzyl alcohol, puriss., meets analytical specification of Ph. Eur., BP, NF, 99-100.5% (GC)
Supelco
Benzyl alcohol, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Benzyl alcohol, European Pharmacopoeia (EP) Reference Standard
Sigma-Aldrich
Water, for embryo transfer, sterile-filtered, BioXtra, suitable for mouse embryo cell culture