Premium
Efficient One‐Pot Synthesis of Multi‐Substituted Dihydrofurans by Ruthenium(II)‐Catalyzed [3+2] Cycloaddition of Cyclic or Acyclic Diazodicarbonyl Compounds with Olefins
Author(s) -
Xia Likai,
Lee Yong Rok
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300245
Subject(s) - chemistry , ruthenium , cycloaddition , triphenylphosphine , regioselectivity , tetrafluoroborate , phosphine , catalysis , chloride , combinatorial chemistry , organic chemistry , medicinal chemistry , ionic liquid
Abstract Ruthenium(II)‐phosphine complexes‐catalyzed [3+2] cycloadditions were conducted to synthesize a variety of dihydrofurans by reactions of cyclic or acyclic diazodicarbonyl compounds with olefins. This method represents a direct and efficient one‐pot synthesis for multi‐substituted dihydrofurans under mild reaction conditions with an excellent regioselectivity. Furthermore, to reduce reaction times and increase yields of dihydrofurans, microwave‐assisted tris(triphenylphosphine)ruthenium(II) chloride/ 1‐butyl‐3‐methylimidazolium tetrafluoroborate {Ru(PPh 3 ) 3 Cl 2 /[Bmim]BF 4 }‐catalyzed reactions were also developed. The synthesized dihydrofurans can be readily converted into biologically interesting tetrahydroindoles.