期刊
ACS CATALYSIS
卷 8, 期 2, 页码 1003-1008出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b03688
关键词
nickel; catalysis; cross-coupling; aliphatic; amides
资金
- NIH-NIGMS [R01 GM117016]
- UCLA Gold Shield Alumnae
- University of California, Los Angeles
- National Science Foundation [DGE-1144087]
- Foote Family
- NSF [CHE-1048804]
- National Center for Research Resources [S10RR025631]
We report the Ni-catalyzed Suzuki Miyaura coupling of aliphatic amide derivatives. Prior studies have shown that aliphatic amide derivatives can undergo Ni-catalyzed carbon heteroatom bond formation but that Ni-mediated C-C bond formation using aliphatic amide derivatives has remained difficult. The coupling disclosed herein is tolerant of considerable variation with respect to both the amide-based substrate and the boronate coupling partner and proceeds in the presence of heterocycles and epimerizable stereocenters. Moreover, a gram-scale Suzuki-Miyaura coupling/Fischer indolization sequence demonstrates the ease with which unique polyheterocyclic scaffolds can be constructed, particularly by taking advantage of the enolizable ketone functionality present in the cross-coupled product. The methodology provides an efficient means to form C-C bonds from aliphatic amide derivatives using nonprecious-metal catalysis and offers a general platform for the heteroarylation of aliphatic acyl electrophiles.
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