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Metal‐Free Arylation‐Lactonization Sequence of γ ‐Alkenoic Acids Using Anilines as Aryl Radical Precursors
Author(s) -
FelipeBlanco Diego,
GonzalezGomez Jose C.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901679
Subject(s) - chemistry , radical , aryl , catalysis , salicylic acid , reaction mechanism , sequence (biology) , reaction conditions , metal , organic chemistry , combinatorial chemistry , biochemistry , alkyl
The presence of salicylic acid (10 mol‐%) and H 2 O (10 equiv.) significantly improves the arylation‐lactonization sequence of γ ‐alkenoic acids with in situ formed diazonium salts (from bench stable anilines). The reaction is finished in less than 5 h without thermal or photochemical activation, giving access to a variety of γ,γ ‐disubstituted butyrolactones. The protocol is user‐friendly and can be used at gram‐scale or adapted to transform alkenols into phthalanes. Control experiments revealed that aryl radicals participate in the reaction and a plausible mechanism is proposed to include this and other mechanistic investigations, for the catalyzed and the background reaction.