Iron-Catalyzed Cross-Electrophile Coupling for the Formation of All-Carbon Quaternary Centers.

Autor: Pace AL; Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States., Xu F; Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States., Liu W; Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States., Lavagnino MN; Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States., MacMillan DWC; Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2024 Dec 04; Vol. 146 (48), pp. 32925-32932. Date of Electronic Publication: 2024 Nov 20.
DOI: 10.1021/jacs.4c14942
Abstrakt: Quaternary carbon centers are desirable targets for drug discovery and complex molecule synthesis, yet the synthesis of these motifs within traditional cross-coupling paradigms remains a significant challenge due to competing β-hydride elimination pathways. In contrast, the bimolecular homolytic substitution (S H 2) mechanism offers a unique and attractive alternative pathway. Metal porphyrin complexes have emerged as privileged catalysts owing to their ability to selectively form primary metal-alkyl complexes, thereby eliminating the challenges associated with tertiary alkyl complexation with a metal center. Herein, we report an iron-catalyzed cross-electrophile coupling of tertiary bromides and primary alkyl electrophiles for the formation of all-carbon quaternary centers through a biomimetic S H 2 mechanism.
Databáze: MEDLINE
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