111477-34-0Relevant academic research and scientific papers
Oxime-Derived Palladium Complexes as Very Efficient Catalysts for the Heck-Mizoroki Reaction
Alonso, Diego A.,Najera, Carmen,Pacheco, Ma. Carmen
, p. 172 - 183 (2007/10/03)
Oxime-derived, chloro-bridged palladacycles 16 are efficient complexes for the Heck vinylation of aryl halides. The isolated catalysts are thermally stable, not sensitive to air or moisture and easily accessible from inexpensive starting materials. The reaction can be performed under aerobic conditions, with aryl iodides, bromides and chlorides with acrylic esters and olefins displaying turnover numbers (TON) of up to 1010 for phenyl iodide and turnover frequencies (TOF) of 1.4 × 108 h-1. Deactivated aryl bromides undergo the Heck reaction with styrene with TON and TOF values up to 97,000 and 6063 h-1, respectively. Even aryl chlorides undergo the coupling reaction with olefins with TON up to 920. Complexes 16 catalyze the synthesis of 2,3-disubstituted indenones and indoles in good yields via annulation reaction of internal alkynes with o-bromoor o-chlorobenzaldehyde and o-iodoaniline, respectively.
Condensed heteroaromatic ring systems. XX. Palladium-catalyzed carbonylative coupling of iodobenzenes with (Z)-1-ethoxy-2-(tributylstannyl)ethene
Sakamoto,Yasuhara,Kondo,Yamanaka
, p. 1137 - 1139 (2007/10/02)
Palladium-catalyzed cross-coupling reaction of iodobenzene and its 4-substituted derivatives, except for 4-nitroiodobenzene, with (Z)-1-ethoxy-2-(tributylstannyl)ethene under a carbon monoxide atmosphere (5 atm) gave the corresponding (E)-3-ethoxy-1-arylprop-2-en-1-ones in considerable yields. Syntheses of chromone and 4(1H)-quinolinone were accomplished by application of this method to 2-(methoxymethoxy)iodobenzene and ethyl 2-iodophenylcarbanylate, respectively. The results obtained on the carbonylative coupling reaction of halopyridines are also described.
Condensed heteroaromatic ring systems. XVII. Palladium-catalyzed cross-coupling reaction of aryl bromides with (Z)-1-ethoxy-2-tributylstannylethene and its utilization for construction of condensed heteroaromatics
Sakamoto,Kondo,Yasuhara,Yamanaka
, p. 1877 - 1886 (2007/10/02)
The palladium-catalyzed cross-coupling reaction of bromobenzenes or bromoheteroarenes such as pyridine, thiophene, indole with (Z)-1-ethoxy-2-tributylstannylethene gives good yields of the corresponding (Z)-1-ethoxy-2-(aryl and heteroaryl)ethenes. This method is effective for introducing an ethoxyethenyl group into an aromatic and heteroaromatic ring and is proved to have versatile utility for the construction of benzo[b]furan, indole, isocoumarin rings 2-bromophenol, 2-bromoaniline, and 2-bromobenzoate derivatives.
REACTION OF ARYL HALIDES WITH (Z)-1-ETHOXY-2-TRIBUTYLSTANNYLETHENE: A VERSATILE METHOD FOR THE INTRODUCTION OF 2-ETHOXYETHENYL GROUP INTO AROMATIC NUCLEI
Sakamoto, Takao,Kondo, Yoshinori,Yasuhara, Akito,Yamanaka, Hiroshi
, p. 219 - 221 (2007/10/02)
The reaction of 4-substituted bromobenzenes, except for 4-bromophenol and 4-bromoaniline, with (Z)-1-ethoxy-2-tributylstannylethene is well prompted by the catalytic action of dichlorobis(triphenylphosphine)palladium in dimethylformamide in the presence o
