Reactions of Fluoroalkanes with Mg−Mg Bonds: Scope, sp3C−F/sp2C−F Coupling and Mechanism
G Coates, BJ Ward, C Bakewell… - … A European Journal, 2018 - Wiley Online Library
G Coates, BJ Ward, C Bakewell, AJP White, MR Crimmin
Chemistry–A European Journal, 2018•Wiley Online LibraryAbstract sp3C− F Bonds of fluoroalkanes (7 examples; 1°, 2° and 3°) undergo addition to a
low‐valent Mg− Mg species generating reactive organomagnesium reagents. Further
reactions with a series of electrophiles results in a net C− F to C− B, C− Si, C− Sn or C− C
bond transformation (11 examples, diversity). The new reactivity has been exploited in an
unprecedented one‐pot magnesium‐mediated coupling of sp3C− F and sp2C− F bonds.
Calculations suggest that the sp3C− F bond activation step occurs by frontside nucleophilic …
low‐valent Mg− Mg species generating reactive organomagnesium reagents. Further
reactions with a series of electrophiles results in a net C− F to C− B, C− Si, C− Sn or C− C
bond transformation (11 examples, diversity). The new reactivity has been exploited in an
unprecedented one‐pot magnesium‐mediated coupling of sp3C− F and sp2C− F bonds.
Calculations suggest that the sp3C− F bond activation step occurs by frontside nucleophilic …
Abstract
sp3C−F Bonds of fluoroalkanes (7 examples; 1°, 2° and 3°) undergo addition to a low‐valent Mg−Mg species generating reactive organomagnesium reagents. Further reactions with a series of electrophiles results in a net C−F to C−B, C−Si, C−Sn or C−C bond transformation (11 examples, diversity). The new reactivity has been exploited in an unprecedented one‐pot magnesium‐mediated coupling of sp3C−F and sp2C−F bonds. Calculations suggest that the sp3C−F bond activation step occurs by frontside nucleophilic attack of the Mg−Mg reagent on the fluoroalkane.
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