Palladium-catalyzed one-pot three- or four-component coupling of aryl iodides, alkynes, and amines through C-N bond cleavage: efficient synthesis of indole derivatives.
An efficient synthesis of N-substituted indole derivatives was realized by combining the Pd-catalyzed one-pot multicomponent coupling approach with cleavage of the C(sp(3))-N bonds. Three or four components of aryl iodides, alkynes, and amines were involved in this coupling process. The cyclopentadiene-phosphine ligand showed high efficiency. A variety of aryl iodides, including cyclic and acyclic tertiary amino aryl iodides, and substituted 1-bromo-2-iodobenzene derivatives could be used. Both symmetric and unsymmetric alkynes substituted with alkyl, aryl, or trimethylsilyl groups could be applied. Cyclic secondary amines such as piperidine, morpholine, 4-methylpiperidine, 1-methylpiperazine, 2-methylpiperidine, and acyclic amines including secondary and primary amines all showed good reactivity. Further application of the resulting indole derivatives was demonstrated by the synthesis of benzosilolo[2,3-b]indole.
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (China), Fax: (+86) 10-62751708.
Wei
W
Hao
Weizhi
W
Geng
Wen-Xiong
WX
Zhang
Zhenfeng
Z
Xi
D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry
D000480:Alkynes; D000588:Amines; D006571:Heterocyclic Compounds; D007211:Indoles; D007454:Iodides; D008024:Ligands; D010720:Phosphines; C000592960:benzosilolo(2,3-b)indole; D010165:Palladium; C030374:indole; C044646:phosphine
cleavage reactions; indoles; multicomponent reactions; palladium; synthetic methods