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

264 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.\}",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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

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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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