Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents

Tie Gen Chen, Haolin Zhang, Pavel K. Mykhailiuk, Rohan R. Merchant, Courtney A. Smith, Tian Qin, Phil S. Baran

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

This work bridges a gap in the cross-coupling of aliphatic redox-active esters with aryl zinc reagents. Previously limited to primary, secondary, and specialized tertiary centers, a new protocol has been devised to enable the coupling of general tertiary systems using nickel catalysis. The scope of this operationally simple method is broad, and it can be used to simplify the synthesis of medicinally relevant motifs bearing quaternary centers.

Original languageEnglish (US)
Pages (from-to)2454-2458
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number8
DOIs
StatePublished - Feb 18 2019
Externally publishedYes

Fingerprint

Bearings (structural)
Carboxylic Acids
Nickel
Carboxylic acids
Catalysis
Zinc
Esters
Oxidation-Reduction

Keywords

  • decarboxylative radical coupling
  • nickel catalysis
  • quaternary centers
  • redox-active esters
  • tertiary acids

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents. / Chen, Tie Gen; Zhang, Haolin; Mykhailiuk, Pavel K.; Merchant, Rohan R.; Smith, Courtney A.; Qin, Tian; Baran, Phil S.

In: Angewandte Chemie - International Edition, Vol. 58, No. 8, 18.02.2019, p. 2454-2458.

Research output: Contribution to journalArticle

Chen, Tie Gen ; Zhang, Haolin ; Mykhailiuk, Pavel K. ; Merchant, Rohan R. ; Smith, Courtney A. ; Qin, Tian ; Baran, Phil S. / Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents. In: Angewandte Chemie - International Edition. 2019 ; Vol. 58, No. 8. pp. 2454-2458.
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