TY  - JOUR
A1  - Schmidt, Bernd
A1  - Wolf, Felix
A1  - Brunner, Heiko
T1  - Styrylsulfonates and -Sulfonamides through Pd-Catalysed Matsuda-Heck Reactions of Vinylsulfonic Acid Derivatives and Arenediazonium Salts
JF  - European journal of organic chemistry
N2  - Arene diazonium salts undergo Matsuda-Heck reactions with vinylsulfonates and -sulfonamides to give styrylsulfonic acid derivatives in high to excellent yields and with high to excellent selectivities. By quantifying the evolution of nitrogen over time in a gas-meter apparatus, the reactivities of ethylvinylsulfonate and the benchmark olefin methyl acrylate were compared for an electron-rich and an -deficient arene diazonium salt. Tertiary sulfonamides react in Matsuda-Heck couplings with high conversions, but require long reaction times, which prevents the determination of kinetic data through the measurement of nitrogen evolution. Secondary sulfonamides were found to be unreactive. From these results, the following order of reactivity could be deduced: H2C=CHCO2Me > H2C=CHSO2OEt > H2C=CHSO2N(Me)Bn >> H2C=CHSO2NHBn. Through the Matsuda-Heck coupling of 5-indolyldiazonium salt and a tertiary vinylsulfonamide, the synthesis of the C-5-substituted indole part of the antimigraine drug naratriptan was accomplished in high yield.
KW  - Homogeneous catalysis
KW  - Cross-coupling
KW  - Palladium
KW  - Sulfonamides
KW  - Alkenes
KW  - Drug design
Y1  - 2016
U6  - https://doi.org/10.1002/ejoc.201600469
SN  - 1434-193X
SN  - 1099-0690
SP  - 2972
EP  - 2982
PB  - Wiley-VCH
CY  - Weinheim
ER  -