- 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
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Product Description
Sigma-Aldrich
Water, for embryo transfer, sterile-filtered, BioXtra, suitable for mouse embryo cell culture
Pure Water Density Standard, UKAS ISO/IEC17025 and ISO Guide 34 certified, density: 0.9982 g/mL at 20 °C, density: 0.9970 g/mL at 25 °C
Pure Water Density Standard, UKAS ISO/IEC17025 and ISO Guide 34 certified, density: 0.9982 g/mL at 20 °C, density: 0.9970 g/mL at 25 °C
Supelco
Benzyl alcohol, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland