Palladium-catalyzed functionalization of indoles with 2-acetoxymethyl-substituted electron-deficient alkenes.
New functionalizations of indoles via palladium-catalyzed reaction of indoles and 2-acetoxymethyl-substituted electron-deficient alkenes are reported. It was found that for N-protected indoles the reaction proceeded smoothly in the presence of 5 mol % of Pd(acac)2 and 10 mol % of PPh3 at 80 degrees C in HOAc, while for N-unprotected indoles, the reaction was carried out by using 5 mol % of Pd(dba)2 or 2.5 mol % of Pd2(dba)3.CHCl3 with 10 mol % of 2,2'-bipyridine as the catalyst in toluene. This strategy allows the selective installation of electron-deficient olefin functionality at the 3-position of indoles, which might be difficult to obtain by other methods and can be further elaborated.
Ma
Shengming
S
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, PR China. masm@mail.sioc.ac.cn
Yu
Shichao
S
Peng
Zhihua
Z
Guo
Hao
H
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004583:Electrons; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D007211:Indoles; D008024:Ligands; D009942:Organometallic Compounds; D010165:Palladium