Cu-Catalyzed Cross-Dehydrogenative Coupling of Heteroaryl C(sp2)-H and Tertiary C(sp3)-H Bonds for the Construction of All-Carbon Triaryl Quaternary Centers

Zhi Tang; Zhili Liu; Zhou Tong; Zhihui Xu; Chak-Tong Au; Renhua Qiu; Nobuaki Kambe

doi:10.1021/acs.orglett.9b01755

Cu-Catalyzed Cross-Dehydrogenative Coupling of Heteroaryl C(sp²)-H and Tertiary C(sp³)-H Bonds for the Construction of All-Carbon Triaryl Quaternary Centers

Org Lett. 2019 Jul 5;21(13):5152-5156. doi: 10.1021/acs.orglett.9b01755. Epub 2019 Jun 18.

Authors

Zhi Tang¹, Zhili Liu¹, Zhou Tong¹, Zhihui Xu¹, Chak-Tong Au^{1

2}, Renhua Qiu¹, Nobuaki Kambe^{1

3}

Affiliations

¹ State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering , Hunan University , Changsha 410082 , P.R. China.
² College of Chemistry and Chemical Engineering , Hunan Institute of Engineering , Xiangtan 411104 , P.R. China.
³ Department of Applied Chemistry, Graduate School of Engineering , Osaka University , Suita , Osaka 565-0871 , Japan.

PMID: 31247797
DOI: 10.1021/acs.orglett.9b01755

Abstract

A Cu-catalyzed protocol for cross-dehydrogenative coupling of benzofuranones with quinolines, indoles, carbazoles, and thiophene, which furnishes highly functionalized 3,3-diaryl benzofuranones bearing a three aryl quaternary carbon center at the C3 position in good yields, has been developed. A radical mechanism is proposed.