期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 42, 页码 11298-11301出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405982
关键词
alpha-arylation; C-H functionalization; iodonium-Claisen rearrangement; dehydrogenative C-C coupling; hypervalent iodine
资金
- ICIQ, MICINN [CTQ2011-22649]
- MEC [Cons. Ing. CSD2007-00006]
- Generalitat de Catalunya [2014SGR1192, 2014SGR1105]
- China Scholarship Council
- MINECO [CTQ2013-46705-R]
- Severo Ochoa Excellence Accreditation [SEV-2013-0319]
The -arylation of carbonyl compounds is generally accomplished under basic conditions, both under metal catalysis and via aryl transfer from the diaryl (3)-iodanes. Here, we describe an alternative metal-free -arylation using ArI(O2CCF3)(2) as the source of a 2-iodoaryl group. The reaction is applicable to activated ketones, such as -cyanoketones, and works with substituted aryliodanes. This formal CH functionalization reaction is thought to proceed through a [3,3] rearrangement of an iodonium enolate. The final -(2-iodoaryl)ketones are versatile synthetic building blocks.
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