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[2+2+1+1] Cycloaddition for de novo Synthesis of Densely Functionalized Phenols |
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| Authors: | Dr. Wei Wei Ka Key Cheung Dr. Ran Lin Lam Cheung Kong Ka Lok Chan Dr. Herman H. Y. Sung Prof. Dr. Ian D. Williams Prof. Dr. Rongbiao Tong Prof. Dr. Zhenyang Lin Prof. Dr. Guochen Jia |
| Affiliation: | 1. 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.;2. 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;3. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China |
| 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. |
| Keywords: | Alkynes Benzannulation Reaction Metallacyclobutadienes Phenol Rhenium |