Metal-free regioselective oxidative biaryl coupling leading to head-to-tail bithiophenes: reactivity switching, a concept based on the iodonium(III) intermediate

Koji Morimoto; Nobutaka Yamaoka; Chieko Ogawa; Tomofumi Nakae; Hiromichi Fujioka; Toshifumi Dohi; Yasuyuki Kita

doi:10.1021/ol101498r

Metal-free regioselective oxidative biaryl coupling leading to head-to-tail bithiophenes: reactivity switching, a concept based on the iodonium(III) intermediate

Org Lett. 2010 Sep 3;12(17):3804-7. doi: 10.1021/ol101498r.

Authors

Koji Morimoto¹, Nobutaka Yamaoka, Chieko Ogawa, Tomofumi Nakae, Hiromichi Fujioka, Toshifumi Dohi, Yasuyuki Kita

Affiliation

¹ College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan.

PMID: 20690618
DOI: 10.1021/ol101498r

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Iodine / chemistry*
Molecular Structure
Oxidation-Reduction
Stereoisomerism
Thiophenes / chemical synthesis*
Thiophenes / chemistry*

Substances

Thiophenes
Iodine