期刊
ACS CATALYSIS
卷 8, 期 12, 页码 11368-11376出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b03436
关键词
tandem catalysis; C-H activation; C-O cleavage; nickel; carbodicarbene; cross-coupling
资金
- Ministry of Science & Technology of Taiwan [MOST-104-2628-M-001-005-MY4]
- Academia Sinica Career Development Award [104-CDA-M08]
- Academia Sinica Investigator Award [AS-IA-108-M04]
- Nanjing Tech University [39837123]
- SICAM Fellowship from Jiangsu National Synergetic Innovation Center for Advanced Materials
- National Natural Science Foundation of China [21828101, 21703099]
- Natural Science Foundation of Jiangsu Province for Youth [BK20170964]
Inert aryl methyl ethers as coupling components via C-O activation have been established with a Ni catalyst for C-H activation of heteroarene. The key to simultaneous C-H/C-O bond activation is the use of sterically demanding o-tolylMgBr. The protocol is effective for a wide scope of substrates including naphthyl methyl ethers, anisoles, and a variety of other heteroarene derivatives. Detailed mechanistic studies indicated that the C-O cleavage is assisted via synergistic effect of nickel and Grignard reagent in this C-H/C-O reaction, which is supported by DFT calculation. At this stage, single-electron transfer can be ruled out as a main operative process for this tandem strategy.
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