Sc(OTf)3-catalyzed efficient synthesis of beta,beta-bis(indolyl) ketones by the double indolylation of acetic acid 2-methylene-3-oxobutyl ester.
In the presence of 5 mol% Sc(OTf)3, double indolylation of acetic acid 2-methylene-3-oxo-butyl ester with differently substituted indoles readily afforded beta,beta-bis(indolyl) ketones. The reaction may proceed via a Sc(OTf)3-catalyzed SN2'-type substitution and subsequent conjugate addition.
Ma
Shengming
S
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, PR China. masm@mail.sioc.ac.cn
Yu
Shichao
S
Peng
Zhihua
Z
D019342:Acetic Acid / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D007211:Indoles / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D012538:Scandium / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
D004952:Esters; D007211:Indoles; D007659:Ketones; D019342:Acetic Acid; D012538:Scandium