期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 6, 页码 2771-2774出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo500222d
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资金
- National Science Foundation [NSF CHE 1058075]
- CBBI Program at the University of Notre Dame (NIGMS) [T32-075762]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1058075] Funding Source: National Science Foundation
The SET-induced biaryl cross-coupling reaction is established as the first example of a Grignard S(RN)1 reaction. The reaction is examined within the mechanistic framework of dissociative electron transfer in the presence of a Lewis acid. DFT calculations show that the reaction proceeds through a radical intermediate in the form of an Mg ion-radical cage, which eludes detection in trapping experiments by reacting quickly to form an MgPh2 radical anion intermediate. A new mechanism is proposed.
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