Mild, Redox-Neutral Formylation of Aryl Chlorides through the Photocatalytic Generation of Chlorine Radicals

Matthew K. Nielsen; Benjamin J. Shields; Junyi Liu; Michael J. Williams; Michael J. Zacuto; Abigail G. Doyle

doi:10.1002/anie.201702079

Mild, Redox-Neutral Formylation of Aryl Chlorides through the Photocatalytic Generation of Chlorine Radicals

Matthew K. Nielsen, Benjamin J. Shields, Junyi Liu, Michael J. Williams, Michael J. Zacuto, Abigail G. Doyle

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

175 Scopus citations

Abstract

We report a redox-neutral formylation of aryl chlorides that proceeds through selective 2-functionalization of 1,3-dioxolane through nickel and photoredox catalysis. This scalable benchtop approach provides a distinct advantage over traditional reductive carbonylation in that no carbon monoxide, pressurized gas, or stoichiometric reductant is employed. The mild conditions give unprecedented scope from abundant and complex aryl chloride starting materials.

Original language	English (US)
Pages (from-to)	7191-7194
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	25
DOIs	https://doi.org/10.1002/anie.201702079
State	Published - Jun 12 2017

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

Keywords

C−H functionalization
formylation
nickel
photocatalysis
redox reactions

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10.1002/anie.201702079

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title = "Mild, Redox-Neutral Formylation of Aryl Chlorides through the Photocatalytic Generation of Chlorine Radicals",

abstract = "We report a redox-neutral formylation of aryl chlorides that proceeds through selective 2-functionalization of 1,3-dioxolane through nickel and photoredox catalysis. This scalable benchtop approach provides a distinct advantage over traditional reductive carbonylation in that no carbon monoxide, pressurized gas, or stoichiometric reductant is employed. The mild conditions give unprecedented scope from abundant and complex aryl chloride starting materials.",

keywords = "C−H functionalization, formylation, nickel, photocatalysis, redox reactions",

author = "Nielsen, {Matthew K.} and Shields, {Benjamin J.} and Junyi Liu and Williams, {Michael J.} and Zacuto, {Michael J.} and Doyle, {Abigail G.}",

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T1 - Mild, Redox-Neutral Formylation of Aryl Chlorides through the Photocatalytic Generation of Chlorine Radicals

AU - Nielsen, Matthew K.

AU - Shields, Benjamin J.

AU - Liu, Junyi

AU - Williams, Michael J.

AU - Zacuto, Michael J.

AU - Doyle, Abigail G.

PY - 2017/6/12

Y1 - 2017/6/12

N2 - We report a redox-neutral formylation of aryl chlorides that proceeds through selective 2-functionalization of 1,3-dioxolane through nickel and photoredox catalysis. This scalable benchtop approach provides a distinct advantage over traditional reductive carbonylation in that no carbon monoxide, pressurized gas, or stoichiometric reductant is employed. The mild conditions give unprecedented scope from abundant and complex aryl chloride starting materials.

AB - We report a redox-neutral formylation of aryl chlorides that proceeds through selective 2-functionalization of 1,3-dioxolane through nickel and photoredox catalysis. This scalable benchtop approach provides a distinct advantage over traditional reductive carbonylation in that no carbon monoxide, pressurized gas, or stoichiometric reductant is employed. The mild conditions give unprecedented scope from abundant and complex aryl chloride starting materials.

KW - C−H functionalization

KW - formylation

KW - nickel

KW - photocatalysis

KW - redox reactions

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

Mild, Redox-Neutral Formylation of Aryl Chlorides through the Photocatalytic Generation of Chlorine Radicals

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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