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Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles.

ABSTRACT: Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Brønsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive and convenient methods should find application in the formation of esters in complex substrates.

SUBMITTER: Mahajani NS

PROVIDER: S-EPMC6597275 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles.

Mahajani Nivedita S NS Meador Rowan I L RIL Smith Tomas J TJ Canarelli Sarah E SE Adhikari Arijit A AA Shah Jigisha P JP Russo Christopher M CM Wallach Daniel R DR Howard Kyle T KT Millimaci Alexandra M AM Chisholm John D JD

The Journal of organic chemistry 20190530 12

Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Brønsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive and convenient methods should find application in the formation of esters in ...[more]

PMID: 31117564

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