Journal
ACS CATALYSIS
Volume 8, Issue 8, Pages 7484-7488Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b02302
Keywords
gold catalysis; mechanism; C-H arylation; rate-attenuation analysis; ortho substituents
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Funding
- AstraZeneca
- CatSci
- European Research Council under the European Union [340163]
- European Research Council (ERC) [340163] Funding Source: European Research Council (ERC)
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ortho-Substituted aryl silanes have previously been found to undergo much slower Au-catalyzed intermolecular arylation than their m,p-substituted isomers, with many examples failing to undergo turnover at all. A method to indirectly quantify the rates of C-Si auration of o-substituted aryl silanes, under conditions of turnover, has been developed. All examples are found to undergo very efficient C-Si auration, indicative that it is the subsequent C-H auration that is inhibited by the ortho substituent. A simple Ar-Au conformational model suggests that C-H auration can be accelerated by chelation. A series of ortho-functionalized aryl silanes are shown to undergo efficient arylation.
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