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Alkynylation of Tertiary Cycloalkanols via Radical C-C Bond Cleavage: A Route to Distal Alkynylated Ketones

Shun Wang, Li-Na Guo, Hua Wang and Xin-Hua Duan*

*Department of Chemistry, School of Science and MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi’an Jiaotong University, Xi’an 710049, China, Email:

S. Wang, L.-N. Guo, H. Wang, X.-H. Duan, Org. Lett., 2015, 17, 4798-4801.

DOI: 10.1021/acs.orglett.5b02353 (free Supporting Information)

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An efficient Na2S2O8-promoted radical coupling of tertiary cycloalkanols with alkynyl hypervalent iodide reagents provides β-, γ- and δ-alkynylated ketones via C-C bond cleavage. This tandem ring-opening/alkynylation procedure offers mild conditions and wide substrate scope.

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Key Words

alkynylation, carbonyl compounds (β-substituted, γ-substituted), sodium peroxydisulfate

ID: J54-Y2015