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Efficient and Functional‐Group‐Tolerant Synthesis of Substituted Furans through the Pd‐Catalyzed 5‐ exo ‐ dig Cyclization/Coupling of γ‐Acetylenic β‐Keto Esters with (Hetero)Aryl Bromides
Author(s) -
Kołodziejczyk Agata,
Chaładaj Wojciech
Publication year - 2018
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.201800046
Subject(s) - chemistry , functional group , isomerization , aryl , dig , catalysis , medicinal chemistry , coupling reaction , double bond , combinatorial chemistry , organic chemistry , alkyl , polymer , computer security , computer science
We report an efficient protocol for the synthesis of 2,3,5‐trisubstituted furans through the reaction of readily available γ‐acetylenic β‐keto esters with aryl and heteroaryl bromides. The reaction, which involves a 5‐ exo ‐ dig cyclization, coupling, and isomerization of a double bond, proceeds smoothly with very low catalyst loading (0.1 mol‐%), and shows excellent functional‐group tolerance.