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Chem Asian J. 2018 May 4;13(9):1157-1164. doi: 10.1002/asia.201800211. Epub 2018 Apr 10.

Sulfinate-Salt-Mediated Radical Relay Cyclization of Cyclic Ethers with 2-Alkynylbenzonitriles toward 3-Alkylated 1-Indenones.

Author information

1
School of Chemical Engineering & Technology, China University of Mining and Technology, Xuzhou, 221116, P. R. China.
2
Department of Chemistry, Xuzhou Medical University, Xuzhou, 221004, P. R. China.
3
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116, P. R. China.

Abstract

A new sulfinate salt-mediated radical relay for the completion of C(sp3 )-H bond indenylation of cyclic ethers with readily available 2-alkynylbenzonitriles by combining silver/tert-butyl peroxide (TBHP) was established, providing a wide range of 3-alkylated 1-indenones with generally good yields. Interestingly, the current reaction system can tolerate an S-centered radical and a C-centered radical in one pot, in which the S-centered radical promotes the formation of the C-centered radical to induce a radical cascade without disturbing the reaction process. A reaction mechanism is also proposed based on control experiments.

KEYWORDS:

1-indenones; C(sp3)-H bond functionalization; carbocyclization; cyclic ethers; radical relay

PMID:
29512882
DOI:
10.1002/asia.201800211

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