期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 16, 页码 4949-4952出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201412148
关键词
alkynes; CH activation; enynes; iodine; rhodium
资金
- DFG [NA 955/1-1]
- Fonds der Chemischen Industrie (Sachkostenzuschuss)
- Carl-Zeiss-Stiftung
The first direct alkynylation of 2-vinylphenols was developed. The rationally optimized hypervalent iodine reagent TIPS-EBX* in combination with [(Cp*RhCl2)(2)] as a CH-activating transition metal catalyst enables the construction of a variety of highly substituted 1,3-enynes in high yields of up to 98%. This novel CH activation method shows excellent chemoselectivity and exclusive (Z)-stereoselectivity, and it is also remarkably mild and tolerates a variety of functional groups. Furthermore, synthetic modifications of the resulting 1,3-enynes were demonstrated. To our knowledge, this is the first example for an OH-directed CH alkynylation with hypervalent iodine reagents.
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