Concise Report
Palladium-Catalyzed Oxidative Alkynylation of Allenyl Ketones: Access to 3-Alkynyl Poly-substituted Furans†
Bowen Dou,
Kang Wang,
Jianbo Wang,
Bowen Dou
Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
Search for more papers by this authorKang Wang
Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
Search for more papers by this authorCorresponding Author
Jianbo Wang
Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032 China
E-mail: [email protected]Search for more papers by this authorBowen Dou,
Kang Wang,
Jianbo Wang,
Bowen Dou
Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
Search for more papers by this authorKang Wang
Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
Search for more papers by this authorCorresponding Author
Jianbo Wang
Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032 China
E-mail: [email protected]Search for more papers by this author†
Dedicated to the Memory of Professor Xiyan Lu.
Comprehensive Summary
Furans bearing alkynyl substituents are highly useful in organic synthesis. However, the methodologies to access these important furan derivatives are rather limited. We herein report an efficient synthesis of alkynylated furan derivatives based on Pd-catalyzed oxidative cross-coupling reaction between allenyl ketones and terminal alkynes. This novel synthesis of alkynylated furans with wide substrate scope is operationally simple and tolerates various functional groups. Mechanistically, the formation of the palladium carbene through cycloisomerization and the subsequent alkynyl migratory insertion are proposed as the key steps in the transformation. The reaction reported in this paper further demonstrates the generality of the carbene-based cross coupling.
Supporting Information
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Appendix S1: Supporting Information |
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