Synergistic Pd/Cu-catalyzed regio- and stereoselective cascade Heck cyclization/borylation/cross-coupling |
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| Institution: | 1. National Key Laboratory of Green Pesticide, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, College of Plant Protection, South China Agricultural University, Guangzhou 510642, China;2. Henry Fok School of Biology and Agriculture, Shaoguan University, Shaoguan 512005, China;3. College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China;1. Key Lab for Colloid and Interface Chemistry of Education Ministry, Shandong University, Jinan 250100, China;2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China;3. Functional Molecules of Zhejiang Province, School of Science, Westlake University, Hangzhou 310024, China;4. Key Laboratory of Organic Chemistry in Jiangxi Province, Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, China;1. School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou 221116, China;2. Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Pharmacy, Changzhou University, Changzhou 213164, China;1. College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, China;2. Key Laboratory of Chemical Biology of Fujian Province, State Key Laboratory of Physical Chemistry of Solid Surfaces, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China;3. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China |
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| Abstract: | A cooperative Pd/Cu-catalyzed three-component cross-coupling reaction of alkynes, B2Pin2 and alkene-tethered aryl halides is reported. This reaction proceeds under mild conditions and shows broad substrate scope, providing a variety of heterocycles containing tetrasubstituted alkenylboronate moieties in synthetically useful yields with excellent chemoselectivity and regioselectivity. This transformation features the catalytic generation of β-borylalkenylcopper intermediates and their use in Pd-catalyzed Heck cyclization/cross-couplings. An enantioselective cascade cyclization/cross-coupling process has also been developed for the synthesis of enantiomerically enriched oxindole bearing a tetrasubstituted alkenylboronate moiety. |
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