期刊
ORGANIC LETTERS
卷 16, 期 1, 页码 62-65出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol403020s
关键词
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资金
- National Science Foundation [IR/D, CHE 1111406, CHE-0963450]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1111406, 0963450] Funding Source: National Science Foundation
The addition of BuLi, Bu3MgLi, Et2ZnBuLi, or Me2CuLi to alpha-arylthioalkanenitriles triggers an arylthio-metal exchange. NMR spectroscopic analyses implicate organometallic attack on sulfur forming a three-coordinate sulfidate as the key intermediate. Electrophilic trapping affords tertiary and quaternary nitriles in high yield. The method addresses the challenge of improving the functional group tolerance and preventing polyalkylations.
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