Exploiting Carbonyl Groups to Control Intermolecular Rhodium-Catalyzed Alkene and Alkyne Hydroacylation
نویسندگان
چکیده
منابع مشابه
2-Aminobenzaldehydes as Versatile Substrates for Rhodium-Catalyzed Alkyne Hydroacylation: Application to Dihydroquinolone Synthesis**
Alkene and alkyne hydroacylation reactions are archetypal examples of simple addition processes that display excellent atom economy. Both reactions result in the formation of a new C C bond and deliver synthetically useful carbonylcontaining products. In recent years, there has been considerable interest in converting these processes into synthetically useful transformations. Transition-metal-c...
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We demonstrate that a single Rh(i) complex can promote two mechanistically distinct C-C bond-forming reactions - alkyne hydroacylation and aryl boronic acid conjugate addition - to deliver substituted ketone products from the controlled assembly of three readily available fragments. This is a rare example of a Rh(i)/Rh(iii) cycle and a redox neutral Rh(i) cycle being promoted by a single cataly...
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Cyclobutanones reacted with alkynes in the presence of nickel(0) catalysts to produce cyclohexenones. Oxidative cyclization of the carbonyl group of the cyclobutanone and the alkyne with the nickel(0) was followed by beta-carbon elimination from the resulting oxanickelacyclopentene and subsequent reductive elimination. This reaction achieves a formal alkyne insertion between the carbonyl carbon...
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The rhodium(III)-catalyzed hydroarylation of internal alkynes is described. Good yields are obtained for a variety of alkynes, and excellent regioselectivity is observed for unsymmetrically substituted alkynes. The reaction also gives good yields for a range of arenes. Preliminary mechanistic investigations suggest that this reaction proceeds through arene metalation with the cationic rhodium c...
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2017
ISSN: 0002-7863,1520-5126
DOI: 10.1021/jacs.7b05713