Acyl Fluorides in Late-Transition-Metal Catalysis

Area of Science:

• Organic Chemistry
• Catalysis
• Material Science

Background:

• Acyl fluorides (RCOF) present a unique balance of stability and reactivity in organic synthesis.
• Their moderate electrophilicity makes them versatile building blocks, unlike more reactive acyl halides.
• Transition-metal catalysis offers efficient pathways for acyl fluoride transformations.

Purpose of the Study:

• To review the state-of-the-art in late-transition-metal-catalyzed reactions involving acyl fluorides.
• To cover both the synthesis and synthetic applications of acyl fluorides.
• To highlight the diverse bond-forming reactions enabled by acyl fluorides.

Main Methods:

• Review of literature on late-transition-metal catalysis (Groups 9-11: Co, Rh, Ir, Ni, Pd, Cu).
• Analysis of reactions involving acyl C-F bond cleavage.
• Categorization of transformations based on bond formation (C-C, C-H, C-B, C-F).

Main Results:

• Acyl fluorides serve as effective "RCO" synthons in coupling reactions.
• They function as "R" sources in decarbonylative coupling processes.
• Acyl fluorides are valuable precursors for C-F bond formation and other functionalizations.

Conclusions:

• Acyl fluorides are highly versatile substrates in modern organic synthesis.
• Late-transition-metal catalysis unlocks a wide range of transformations starting from acyl fluorides.
• The moderate reactivity of acyl fluorides is key to their utility in various catalytic cycles.