期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 16, 页码 6466-6472出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201915875
关键词
dienes; hydrazones; hydroalkylation; regioselectivity; ruthenium
资金
- Canada Research Chair Foundation
- Canadian Foundation for Innovation
- FRQNT Centre in Green Chemistry and Catalysis
- Natural Science and Engineering Research Council of Canada
- Killam Research Fellow of the Canadian Council of Arts
Controlling reaction selectivity is a permanent pursuit for chemists. Regioselective catalysis, which exploits and/or overcomes innate steric and electronic bias to deliver diverse regio-enriched products from the same starting materials, represents a powerful tool for divergent synthesis. Recently, the 1,2-Markovnikov hydroalkylation of 1,3-dienes with simple hydrazones was reported to generate branched allylic compounds when a nickel catalyst was used. As part of the effort, shown here is that a complete switch of Markovnikov to anti-Markovnikov addition is obtained by changing to a ruthenium catalyst, thus providing direct and efficient access to homoallylic products exclusively. Isotopic substitution experiments indicate that no reversible hydro-metallation across the metal-pi-allyl system occurred under ruthenium catalysis. Moreover, this protocol is applicable to the regiospecific hydroalkylation of the distal C=C bond of 1,3-enynes.
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