The regioselective homocoupling of meta-hydroxypyridines with hypervalent iodine(III)

Ping Syun Yang; Mi Ting Tsai; Meng Han Tsai; Chi Wi Ong

doi:10.1002/asia.201403359

The regioselective homocoupling of meta-hydroxypyridines with hypervalent iodine(III)

Chem Asian J. 2015 Apr;10(4):849-52. doi: 10.1002/asia.201403359. Epub 2014 Dec 30.

Authors

Ping Syun Yang¹, Mi Ting Tsai, Meng Han Tsai, Chi Wi Ong

Affiliation

¹ National Sun Yat Sen University, Department of Chemistry, 70 Lienhai Rd., Kaohsiung 80424 (Taiwan).

PMID: 25641879
DOI: 10.1002/asia.201403359

Abstract

The C - H homocoupling of meta-hydroxypyridines with phenyliodine(III) diacetate (PIDA) was carried out in dichloromethane at room temperature in the presence of cesium carbonate. The coupling reaction is highly regioselective with respect to the hydroxy group at the pyridine ring. Comparative control experiments with meta-alkoxypyridine suggest that the meta-hydroxy group at the pyridine ring plays a key role during the homocoupling reaction.

Keywords: 3,3′-dihydroxy-2,2′-bipyridine; direct CC bond formation; hypervalent iodine; meta-hydroxypyridines; metal-free CH homocoupling reaction.