Hydroesterification and difunctionalization of olefins with N-hydroxyphthalimide esters

Lingying Leng; Joseph M. Ready

doi:10.1021/acscatal.1c03969

Hydroesterification and difunctionalization of olefins with N-hydroxyphthalimide esters

Lingying Leng, Joseph M. Ready

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Irradiation of aryl esters of N-hydroxyphthalimides in the presence of unactivated olefins promotes a mild and regioselective hydroesterification. Optimal results are obtained with the aid of fac-Ir(dFppy)₃ in CH₂Cl₂. Terminal and 1,1-disubstituted olefins provide primary esters, and trisubstituted olefins provide secondary esters. The anti-Markovnikov selectivity is consistent with alkyl radical intermediates, which are also indicated by the formation of cyclized products from dienes. Monoacylated diols are formed from trisubstituted and tetrasubstituted olefins in the presence of water.

Original language	English (US)
Pages (from-to)	13714-13720
Number of pages	7
Journal	ACS Catalysis
Volume	11
Issue number	21
DOIs	https://doi.org/10.1021/acscatal.1c03969
State	Published - Nov 5 2021

Keywords

Aminohydroxylation
Anti-Markovnikov
Dihydroxylation
Hydroesterification
Photocatalysis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1021/acscatal.1c03969

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title = "Hydroesterification and difunctionalization of olefins with N-hydroxyphthalimide esters",

abstract = "Irradiation of aryl esters of N-hydroxyphthalimides in the presence of unactivated olefins promotes a mild and regioselective hydroesterification. Optimal results are obtained with the aid of fac-Ir(dFppy)3 in CH2Cl2. Terminal and 1,1-disubstituted olefins provide primary esters, and trisubstituted olefins provide secondary esters. The anti-Markovnikov selectivity is consistent with alkyl radical intermediates, which are also indicated by the formation of cyclized products from dienes. Monoacylated diols are formed from trisubstituted and tetrasubstituted olefins in the presence of water.",

keywords = "Aminohydroxylation, Anti-Markovnikov, Dihydroxylation, Hydroesterification, Photocatalysis",

author = "Lingying Leng and Ready, {Joseph M.}",

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year = "2021",

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T1 - Hydroesterification and difunctionalization of olefins with N-hydroxyphthalimide esters

AU - Leng, Lingying

AU - Ready, Joseph M.

PY - 2021/11/5

Y1 - 2021/11/5

N2 - Irradiation of aryl esters of N-hydroxyphthalimides in the presence of unactivated olefins promotes a mild and regioselective hydroesterification. Optimal results are obtained with the aid of fac-Ir(dFppy)3 in CH2Cl2. Terminal and 1,1-disubstituted olefins provide primary esters, and trisubstituted olefins provide secondary esters. The anti-Markovnikov selectivity is consistent with alkyl radical intermediates, which are also indicated by the formation of cyclized products from dienes. Monoacylated diols are formed from trisubstituted and tetrasubstituted olefins in the presence of water.

AB - Irradiation of aryl esters of N-hydroxyphthalimides in the presence of unactivated olefins promotes a mild and regioselective hydroesterification. Optimal results are obtained with the aid of fac-Ir(dFppy)3 in CH2Cl2. Terminal and 1,1-disubstituted olefins provide primary esters, and trisubstituted olefins provide secondary esters. The anti-Markovnikov selectivity is consistent with alkyl radical intermediates, which are also indicated by the formation of cyclized products from dienes. Monoacylated diols are formed from trisubstituted and tetrasubstituted olefins in the presence of water.

KW - Aminohydroxylation

KW - Anti-Markovnikov

KW - Dihydroxylation

KW - Hydroesterification

KW - Photocatalysis

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ER -

Hydroesterification and difunctionalization of olefins with N-hydroxyphthalimide esters

Abstract

Keywords

ASJC Scopus subject areas

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