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^*

^*Corresponding author for this work

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

250 Citations (Scopus)

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
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
Publication status	Published - 2 Jan 2017
Externally published	Yes

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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",

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

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year = "2017",

month = jan,

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doi = "10.1002/anie.201609662",

language = "English",

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journal = "Angewandte Chemie - International Edition",

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TY - JOUR

T1 - Nickel-Catalyzed Barton Decarboxylation and Giese Reactions

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.

PY - 2017/1/2

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

KW - decarboxylation

KW - esters

KW - nickel catalysis

KW - redox-active

UR - https://www.scopus.com/pages/publications/85007124060

U2 - 10.1002/anie.201609662

DO - 10.1002/anie.201609662

M3 - Article

SN - 1433-7851

VL - 56

SP - 260

EP - 265

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 1

ER -

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

Abstract

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