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 journalArticle

83 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 (PhSiH 3 ) 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 languageEnglish (US)
Pages (from-to)260-265
Number of pages6
JournalAngewandte Chemie - International Edition
Volume56
Issue number1
DOIs
StatePublished - Jan 1 2017
Externally publishedYes

Fingerprint

Alkenes
Nickel
Peptides
Olefins
Hydrogen
Esters
Mathematical transformations
Atoms
Electrons
Oxidation-Reduction
N-hydroxyphthalimide
Decarboxylation
Hot Temperature

Keywords

  • conjugate addition
  • decarboxylation
  • esters
  • nickel catalysis
  • redox-active

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Qin, T., Malins, L. R., Edwards, J. T., Merchant, R. R., Novak, A. J. E., Zhong, J. Z., ... Baran, P. S. (2017). Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms. Angewandte Chemie - International Edition, 56(1), 260-265. https://doi.org/10.1002/anie.201609662

Nickel-Catalyzed Barton Decarboxylation and Giese Reactions : A Practical Take on Classic Transforms. / Qin, Tian; Malins, Lara R.; Edwards, Jacob T.; Merchant, Rohan R.; Novak, Alexander J.E.; Zhong, Jacob Z.; Mills, Riley B.; Yan, Ming; Yuan, Changxia; Eastgate, Martin D.; Baran, Phil S.

In: Angewandte Chemie - International Edition, Vol. 56, No. 1, 01.01.2017, p. 260-265.

Research output: Contribution to journalArticle

Qin, T, Malins, LR, Edwards, JT, Merchant, RR, Novak, AJE, Zhong, JZ, Mills, RB, Yan, M, Yuan, C, Eastgate, MD & Baran, PS 2017, 'Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms', Angewandte Chemie - International Edition, vol. 56, no. 1, pp. 260-265. https://doi.org/10.1002/anie.201609662
Qin, Tian ; Malins, Lara R. ; Edwards, Jacob T. ; Merchant, Rohan R. ; Novak, Alexander J.E. ; Zhong, Jacob Z. ; Mills, Riley B. ; Yan, Ming ; Yuan, Changxia ; Eastgate, Martin D. ; Baran, Phil S. / Nickel-Catalyzed Barton Decarboxylation and Giese Reactions : A Practical Take on Classic Transforms. In: Angewandte Chemie - International Edition. 2017 ; Vol. 56, No. 1. pp. 260-265.
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