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Lewis Acid/Base Adduct FLP – Frustration -> activity

Lewis Acid/Base Adduct FLP – Frustration -> activity. Carbodiphosphoranes ( C(0) ) – high proton affinity ( > amines, phosphines, N-heterocyclic carbenes) - frustration with B(C 6 F 5 ) 3. Reaction with B(C 6 F 5 ) 3

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Lewis Acid/Base Adduct FLP – Frustration -> activity

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  1. Lewis Acid/Base Adduct FLP – Frustration -> activity Carbodiphosphoranes ( C(0) ) – high proton affinity ( > amines, phosphines, N-heterocyclic carbenes) - frustration with B(C6F5)3

  2. Reaction with B(C6F5)3 / H-H Frustration at -78 ℃ (purging H2) (H-H) Adduct at RT

  3. C-O / C-F Ring opening of THF at -78 ℃ (C-O) Ethylene carbonate at -78 ℃ (C-O) 1-fluoropentane at -78 ℃ (C-F) (unprecedented)

  4. Reaction with terminal alkynes / Phenylacetylene at -78 ℃ Basic deprotonation (stronger than tBu3P) Frustration -> nucleophilic attack

  5. Si-H Ph2SiH2 at -78 ℃ EtMe2SiH at -78 ℃ Me3SiOMe at -78 ℃ (C-O) Si-F (X), Si-O (X)

  6. Second proton affinity (-193.4 kcal/mol) (first example of a cationic base in FLP) MeOH at RT (O-H) H-H (X), N-H (X)

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