期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 21, 页码 10960-10967出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo401936v
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资金
- NNSFC [21172096]
- Fundamental Research Funds for the Central Universities [lzujbky-2012-57, lzujbky-2013-ct02]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT1138]
- 111 Project of MoE of China
A room-temperature Ni-catalyzed reductive approach to homocoupling of unactivated primary, secondary, and tertiary alkyl bromides is described. The catalytic system can be easily generated from air-stable and cheap materials and demonstrates broad functional group tolerance, thus allowing facile access to useful dimeric triterpene and lignan-like molecules. Moreover, the dimerization of tertiary bromide 6 1, efficiently establishes sterically hindered vicinal quaternary carbons (C3a and C3a'), which is a key linkage of intriguing bispyrrolo[2,3-b] indoline alkaloids, thereby enabling us to complete the total syntheses of racemic chimonanthine (9) and folicanthine (10). In addition, this dimerization method can be expanded to the highly stereoselective synthesis of bisperhydrofuro[2,3-b]furan (5a) and the dimeric spiroketal 5b, signifying the involvement of possible radical species.
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