Journal
CHEMICAL SCIENCE
Volume 13, Issue 11, Pages 3169-3175Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc06100c
Keywords
-
Categories
Funding
- NSFC [21831002, 22001157, 22193012]
- Ten Thousand Talents Program
- Fundamental Research Funds for the Central Universities [2412021QD007]
- Natural Science Foundation of Shaanxi Province [2020JQ-404]
Ask authors/readers for more resources
The modulation of selectivity of highly reactive carbon radical cross-coupling for the construction of C-C bonds was achieved using N-Heterocyclic carbene (NHC) catalyzed radical transformations. This method successfully realized highly selective cross-coupling between acyl radicals and alkyl radicals for efficient construction of C-C bonds. The study further investigated the cross-coupling reaction of acyl radicals with vinyl radicals, providing valuable insights into the mechanism.
The modulation of selectivity of highly reactive carbon radical cross-coupling for the construction of C-C bonds represents a challenging task in organic chemistry. N-Heterocyclic carbene (NHC) catalyzed radical transformations have opened a new avenue for acyl radical cross-coupling chemistry. With this method, highly selective cross-coupling of an acyl radical with an alkyl radical for efficient construction of C-C bonds was successfully realized. However, the cross-coupling reaction of acyl radicals with vinyl radicals has been much less investigated. We herein describe NHC and visible light-mediated photoredox co-catalyzed radical 1,4-sulfonylacylation of 1,3-enynes, providing structurally diversified valuable tetrasubstituted allenyl ketones. Mechanistic studies indicated that ketyl radicals are formed from aroyl fluorides via the oxidative quenching of the photocatalyst excited state, allenyl radicals are generated from chemo-specific sulfonyl radical addition to the 1,3-enynes, and finally, the key allenyl and ketyl radical cross-coupling provides tetrasubstituted allenyl ketones.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available