Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms

Tian Qin; Lara R. Malins; Jacob T. Edwards; Rohan R. Merchant; Alexander J.E. Novak; Jacob Z. Zhong; Riley B. Mills; Ming Yan; Changxia Yuan; Martin D. Eastgate; Phil S. Baran

doi:10.1002/anie.201609662

Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms

Tian Qin, Lara R. Malins, Jacob T. Edwards, Rohan R. Merchant, Alexander J.E. Novak, Jacob Z. Zhong, Riley B. Mills, Ming Yan, Changxia Yuan, Martin D. Eastgate, Phil S. Baran

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

210 Scopus citations

Abstract

Two named reactions of fundamental importance and paramount utility in organic synthesis have been reinvestigated, the Barton decarboxylation and Giese radical conjugate addition. N-hydroxyphthalimide (NHPI) based redox-active esters were found to be convenient starting materials for simple, thermal, Ni-catalyzed radical formation and subsequent trapping with either a hydrogen atom source (PhSiH₃) or an electron-deficient olefin. These reactions feature operational simplicity, inexpensive reagents, and enhanced scope as evidenced by examples in the realm of peptide chemistry.

Original language	English (US)
Pages (from-to)	260-265
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	1
DOIs	https://doi.org/10.1002/anie.201609662
State	Published - Jan 2 2017
Externally published	Yes

Keywords

conjugate addition
decarboxylation
esters
nickel catalysis
redox-active

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201609662

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title = "Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms",

abstract = "Two named reactions of fundamental importance and paramount utility in organic synthesis have been reinvestigated, the Barton decarboxylation and Giese radical conjugate addition. N-hydroxyphthalimide (NHPI) based redox-active esters were found to be convenient starting materials for simple, thermal, Ni-catalyzed radical formation and subsequent trapping with either a hydrogen atom source (PhSiH3) or an electron-deficient olefin. These reactions feature operational simplicity, inexpensive reagents, and enhanced scope as evidenced by examples in the realm of peptide chemistry.",

keywords = "conjugate addition, decarboxylation, esters, nickel catalysis, redox-active",

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T2 - A Practical Take on Classic Transforms

AU - Qin, Tian

AU - Malins, Lara R.

AU - Edwards, Jacob T.

AU - Merchant, Rohan R.

AU - Novak, Alexander J.E.

AU - Zhong, Jacob Z.

AU - Mills, Riley B.

AU - Yan, Ming

AU - Yuan, Changxia

AU - Eastgate, Martin D.

AU - Baran, Phil S.

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Y1 - 2017/1/2

N2 - Two named reactions of fundamental importance and paramount utility in organic synthesis have been reinvestigated, the Barton decarboxylation and Giese radical conjugate addition. N-hydroxyphthalimide (NHPI) based redox-active esters were found to be convenient starting materials for simple, thermal, Ni-catalyzed radical formation and subsequent trapping with either a hydrogen atom source (PhSiH3) or an electron-deficient olefin. These reactions feature operational simplicity, inexpensive reagents, and enhanced scope as evidenced by examples in the realm of peptide chemistry.

AB - Two named reactions of fundamental importance and paramount utility in organic synthesis have been reinvestigated, the Barton decarboxylation and Giese radical conjugate addition. N-hydroxyphthalimide (NHPI) based redox-active esters were found to be convenient starting materials for simple, thermal, Ni-catalyzed radical formation and subsequent trapping with either a hydrogen atom source (PhSiH3) or an electron-deficient olefin. These reactions feature operational simplicity, inexpensive reagents, and enhanced scope as evidenced by examples in the realm of peptide chemistry.

KW - conjugate addition

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KW - esters

KW - nickel catalysis

KW - redox-active

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Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms

Abstract

Keywords

ASJC Scopus subject areas

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