Access to polysubstituted indoles or benzothiophenes via palladium-catalyzed cross-coupling of furfural tosylhydrazones with 2-iodoanilines or 2-iodothiophenols.
Palladium-catalyzed cross-coupling of furfural tosylhydrazones with 2-iodoanilines or 2-iodothiophenols produces polysubstituted indoles or benzothiophenes, respectively. The reaction proceeds through 2-furylmethylene palladium iodide intermediates, which undergo furan ring opening followed by ring closure to form indoles or benzothiophenes. This reaction will expand the synthetic applications of furfural derivatives.
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China. blyin@scut.edu.cn.
Biaolin
B
Yin
Xiaoyu
X
Zhang
Xiaoting
X
Zhang
Hui
H
Peng
Wen
W
Zhou
Bo
B
Liu
Huanfeng
H
Jiang
D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D006835:Hydrazones / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry; D014105:Tosyl Compounds / Q000737:chemistry*
C552400:2-iodobenzenamine; D000814:Aniline Compounds; D006835:Hydrazones; D007211:Indoles; D009942:Organometallic Compounds; D010636:Phenols; D013876:Thiophenes; D014105:Tosyl Compounds; C088015:benzothiophene; D010165:Palladium