Stereoselective synthesis of 3-alkylideneoxindoles by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents.
A palladium(0)/monophosphine catalyst promotes a cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents to produce stereodefined 3-alkylideneoxindoles. The alkynyl and isocyanato groups undergo oxidative cyclization with Pd(0) to form an oxapalladacycle intermediate. Subsequent transmetalation and reductive elimination afford the product.
Miura
Tomoya
T
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
Toyoshima
Takeharu
T
Takahashi
Yusuke
Y
Murakami
Masahiro
M
D000478:Alkylation; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D017953:Isocyanates / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D000078183:Oxindoles; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D001896:Boron Compounds; D007211:Indoles; D017953:Isocyanates; D000078183:Oxindoles; C022960:2-oxindole; D010165:Palladium