Journal
ACS CATALYSIS
Volume 9, Issue 6, Pages 4862-4866Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b00851
Keywords
pyridines; alkylation; late-stage; phosphonium salts; cross-coupling; cobalt-catalysis; alkyl Negishi
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Funding
- National Institutes of Health (NIGMS) [R01 GM124094]
- Donors of the American Chemical Society Petroleum Research Fund [ACS PRF56878-DNI1]
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Alkylated pyridines are common in pharmaceuticals, and metal catalysis is frequently used to prepare this motif via Csp(2)-Csp(3) coupling processes. We present a cobalt-catalyzed coupling reaction between pyridine phosphonium salts and alkylzinc reagents that can be applied to complex drug-like fragments and for late-stage functionalization of pharmaceuticals. The reaction generally proceeds at room temperature, and 4-position pyridine C-H bonds are the precursors in this strategy. Given the challenges in selectively installing (pseudo)halides in complex pyridines, this two-step process enables sets of molecules to be alkylated that would be challenging using traditional cross-coupling methods.
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