Furan-Based o-Quinodimethanes by Gold-Catalyzed Dehydrogenative Heterocyclization of 2-(1-Alkynyl)-2-alken-1-ones: A Modular Entry to 2,3-Furan-Fused Carbocycles†
Liejin Zhou
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspy
Search for more papers by this authorMingrui Zhang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspy
Search for more papers by this authorDr. Wenbo Li
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspy
Search for more papers by this authorCorresponding Author
Prof. Dr. Junliang Zhang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspy
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspySearch for more papers by this authorLiejin Zhou
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspy
Search for more papers by this authorMingrui Zhang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspy
Search for more papers by this authorDr. Wenbo Li
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspy
Search for more papers by this authorCorresponding Author
Prof. Dr. Junliang Zhang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspy
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspySearch for more papers by this authorFinancial support from the National Natural Science Foundation of China (21372084), 973 Programs (2011CB808600), and the Changjiang Scholars and Innovative Research Team at the University (PCSIRT) is greatly appreciated. We thank Prof. Shengming Ma for helpful discussions.
Graphical Abstract
Caught in a trap: A novel strategy for in situ generation of furan-based ortho-quinodimethanes (o-QDMs) using the title reaction was developed. These furan-based o-QDMs were trapped by electron-deficient olefins and alkynes, thus leading to various 2,3-furan-fused carbocycles in good yields with high diastereo- and regioselectivities. EWG=electron-withdrawing group.
Abstract
A strategy for in situ generation of furan-based ortho-quinodimethanes (o-QDMs) by the gold(I)-mediated dehydrogenative heterocyclization of 2-(1-alkynyl)-2-alken-1-ones in the presence of pyridine N-oxide under mild reaction conditions was developed. These in situ furan-based o-QDMs were trapped by electron-deficient olefins and alkynes, thus furnishing various 2,3-furan-fused carbocycles in good yields with high diastereo- and regioselectivities.
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