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

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.

SUBMITTER: Chen TG

PROVIDER: S-EPMC6391118 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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

Chen Tie-Gen TG Zhang Haolin H Mykhailiuk Pavel K PK Merchant Rohan R RR Smith Courtney A CA Qin Tian T Baran Phil S PS

Angewandte Chemie (International ed. in English) 20190130 8

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. ...[more]

PMID: 30623547

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