Palladium-Catalyzed Bicycloaromatization of <i>o</i>-(Alkynyl)styrenes with Alkynes: Economical Access to Chrysene Derivatives
Bing LiuKey Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha, Hunan 410081, ChinaSen LeiKey Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha, Hunan 410081, ChinaZhendong ChengKey Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha, Hunan 410081, ChinaLiwei ZhouHunan Provincial Key Laboratory of the TCM Agricultural Biogenomics, College of Pharmacy, Changsha Medical University, Changsha, Hunan 410219, ChinaGuobo DengKey Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha, Hunan 410081, ChinaYun LiangKey Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha, Hunan 410081, ChinaYuan YangKey Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha, Hunan 410081, China
2024en
ABI
Abstract
Herein, a palladium-catalyzed bicycloaromatization of o-(alkynyl)styrenes with alkynes is reported. In this protocol, the 6-endo-dig cyclization of o-(alkynyl)styrenes is followed by deprotonation to complete the first cycloaromatization, and then, a regioselective alkyne insertion/C–H activation occurs to achieve the second cycloaromatization, resulting in atom- and step-economical syntheses of polysubstituted chrysenes. Notably, the products can be further used to construct π-extended arenes using the Scholl reaction.
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