[2+2+1+1] Cycloaddition for de novo Synthesis of Densely Functionalized Phenols
Dr. Wei Wei
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
These authors contributed equally to this work.
Search for more papers by this authorKa Key Cheung
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
These authors contributed equally to this work.
Search for more papers by this authorDr. Ran Lin
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Key Laboratory of Biopesticide and Chemical Biology (Ministry of Education), College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou, Fujian, 350002 China
Search for more papers by this authorLam Cheung Kong
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorKa Lok Chan
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorDr. Herman H. Y. Sung
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Ian D. Williams
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Rongbiao Tong
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhenyang Lin
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Guochen Jia
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorDr. Wei Wei
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
These authors contributed equally to this work.
Search for more papers by this authorKa Key Cheung
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
These authors contributed equally to this work.
Search for more papers by this authorDr. Ran Lin
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Key Laboratory of Biopesticide and Chemical Biology (Ministry of Education), College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou, Fujian, 350002 China
Search for more papers by this authorLam Cheung Kong
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorKa Lok Chan
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorDr. Herman H. Y. Sung
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Ian D. Williams
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Rongbiao Tong
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhenyang Lin
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Guochen Jia
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorGraphical Abstract
Densely functionalized phenols can be easily obtained through formal [2+2+1+1] cycloaddition of two different alkynes and two molecules of CO. The new benzannulation strategy allows efficient regioselective installation of up to five different substituents on a phenol ring. The resulting phenols have a substitution pattern different from and complementary to those obtained from Dötz and Danheiser benzannulations.
Abstract
A unique benzannulation strategy for regioselective de novo synthesis of densely functionalized phenols is described. Through metal-mediated formal [2+2+1+1] cycloaddition of two different alkynes and two molecules of CO, a series of densely functionalized phenols were obtained. The benzannulation strategy allows efficient regioselective installation up to five different substituents on a phenol ring. The resulting phenols have a substitution pattern different from those obtained from Dötz and Danheiser benzannulations.
Conflict of interest
The authors declare no conflict of interest.
Open Research
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