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.
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
Tomoya
T
Miura
Takeharu
T
Toyoshima
Yusuke
Y
Takahashi
Masahiro
M
Murakami
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