TY - JOUR
T1 - Iron-Catalyzed Cross-Electrophile Coupling for the Formation of All-Carbon Quaternary Centers
AU - Pace, Andria L.
AU - Xu, Felix
AU - Liu, Wei
AU - Lavagnino, Marissa N.
AU - MacMillan, David W.C.
N1 - Publisher Copyright:
© 2024 American Chemical Society.
PY - 2024/12/4
Y1 - 2024/12/4
N2 - 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 (SH2) 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 SH2 mechanism.
AB - 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 (SH2) 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 SH2 mechanism.
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U2 - 10.1021/jacs.4c14942
DO - 10.1021/jacs.4c14942
M3 - Article
C2 - 39568194
AN - SCOPUS:85209739346
SN - 0002-7863
VL - 146
SP - 32925
EP - 32932
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 48
ER -