Metal-free regioselective oxidative biaryl coupling leading to head-to-tail bithiophenes: reactivity switching, a concept based on the iodonium(III) intermediate.
A new synthetic concept for obtaining unsymmetrical biaryl coupling products by an oxidative method is reported. Our synthetic strategy casts light on the reaction intermediate for switching the reactivity of 3-substituted thiophenes. On the basis of this strategy, a novel direct method for the synthesis of head-to-tail bithiophenes using hypervalent iodine(III) reagents has been developed.
Morimoto
Koji
K
College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan.
Yamaoka
Nobutaka
N
Ogawa
Chieko
C
Nakae
Tomofumi
T
Fujioka
Hiromichi
H
Dohi
Toshifumi
T
Kita
Yasuyuki
Y
D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry*
D013876:Thiophenes; D007455:Iodine