Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, an Organic Photocatalyst, and Visible Light

Trevor C. Sherwood; Hai Yun Xiao; Roshan G. Bhaskar; Eric M. Simmons; Serge Zaretsky; Martin P. Rauch; Robert R. Knowles; T. G.Murali Dhar

doi:10.1021/acs.joc.9b00432

Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, an Organic Photocatalyst, and Visible Light

Trevor C. Sherwood, Hai Yun Xiao, Roshan G. Bhaskar, Eric M. Simmons, Serge Zaretsky, Martin P. Rauch, Robert R. Knowles, T. G.Murali Dhar

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Abstract

An intramolecular arene alkylation reaction has been developed using the organic photocatalyst 4CzIPN, visible light, and N-(acyloxy)phthalimides as radical precursors. Reaction conditions were optimized via high-throughput experimentation, and electron-rich and electron-deficient arenes and heteroarenes are viable reaction substrates. This reaction enables access to a diverse set of fused, partially saturated cores which are of high interest in synthetic and medicinal chemistry.

Original language	English (US)
Pages (from-to)	8360-8379
Number of pages	20
Journal	Journal of Organic Chemistry
Volume	84
Issue number	13
DOIs	https://doi.org/10.1021/acs.joc.9b00432
State	Published - Jul 5 2019

All Science Journal Classification (ASJC) codes

Organic Chemistry

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title = "Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, an Organic Photocatalyst, and Visible Light",

abstract = "An intramolecular arene alkylation reaction has been developed using the organic photocatalyst 4CzIPN, visible light, and N-(acyloxy)phthalimides as radical precursors. Reaction conditions were optimized via high-throughput experimentation, and electron-rich and electron-deficient arenes and heteroarenes are viable reaction substrates. This reaction enables access to a diverse set of fused, partially saturated cores which are of high interest in synthetic and medicinal chemistry.",

author = "Sherwood, {Trevor C.} and Xiao, {Hai Yun} and Bhaskar, {Roshan G.} and Simmons, {Eric M.} and Serge Zaretsky and Rauch, {Martin P.} and Knowles, {Robert R.} and Dhar, {T. G.Murali}",

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doi = "10.1021/acs.joc.9b00432",

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T1 - Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, an Organic Photocatalyst, and Visible Light

AU - Sherwood, Trevor C.

AU - Xiao, Hai Yun

AU - Bhaskar, Roshan G.

AU - Simmons, Eric M.

AU - Zaretsky, Serge

AU - Rauch, Martin P.

AU - Knowles, Robert R.

AU - Dhar, T. G.Murali

PY - 2019/7/5

Y1 - 2019/7/5

N2 - An intramolecular arene alkylation reaction has been developed using the organic photocatalyst 4CzIPN, visible light, and N-(acyloxy)phthalimides as radical precursors. Reaction conditions were optimized via high-throughput experimentation, and electron-rich and electron-deficient arenes and heteroarenes are viable reaction substrates. This reaction enables access to a diverse set of fused, partially saturated cores which are of high interest in synthetic and medicinal chemistry.

AB - An intramolecular arene alkylation reaction has been developed using the organic photocatalyst 4CzIPN, visible light, and N-(acyloxy)phthalimides as radical precursors. Reaction conditions were optimized via high-throughput experimentation, and electron-rich and electron-deficient arenes and heteroarenes are viable reaction substrates. This reaction enables access to a diverse set of fused, partially saturated cores which are of high interest in synthetic and medicinal chemistry.

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Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, an Organic Photocatalyst, and Visible Light

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