1139705-26-2Relevant academic research and scientific papers
O-(Aminosulfonylation) of phenols and an example of slow hydrolytic release
Yang, Baocheng,Sun, Zhexun,Liu, Changzhi,Cui, Yan,Guo, Zhilei,Ren, Yuwei,Lu, Zhijian,Knapp, Spencer
supporting information, p. 6658 - 6661 (2014/12/11)
Sequential replacement of imidazole from sulfonyldiimidazole by phenols and then amines leads to O-arylsulfamate esters. Application of this coupling method to 19 phenols and 6 amines generates a library of 114 sulfamate esters, Ar-OSO2-NR2. A sulfamate based conjugate of ethinyl estradiol was prepared by using the steroid 3-hydroxyl as the phenol component, and an amino amide derived from linoleic acid as the amine. Hydrolysis of this conjugate was studied in aqueous buffer at pH values 2, 5, and 7.4, and (essentially identical) respective half-lives of 6.8, 6.6, and 6.7 days were observed.
Microwave-promoted suzuki-miyaura cross-coupling of aryl imidazolylsulfonates in water
Civicos, Jose F.,Alonso, Diego A.,Najera, Carmen
supporting information, p. 2771 - 2776 (2013/01/15)
Aryl imidazol-1-ylsulfonates are efficiently cross-coupled with potassium aryl- and alkenyltrifluoroborates in neat water under microwave heating (40 W, 110°C) using 0.5 mol% of oxime palladacycle 1a, hexadecyltrimethyl ammonium bromide (CTAB) as additive, and triethylamine as base. Under these simple phosphane-free reaction conditions a wide array of biaryl, stilbene and styrene derivatives has been prepared in good to high yields and with high regio- and diastereoselectivities in only 30 min.
Phosphane-free suzukimiyaura coupling of aryl imidazolesulfonates with arylboronic acids and potassium aryltrifluoroborates under aqueous conditions#
Civicos, Jose Francisco,Gholinejad, Mohammad,Alonso, Diego A.,Najera, Carmen
supporting information; experimental part, p. 907 - 909 (2011/12/05)
Aryl imidazole-1-sulfonates are efficiently cross-coupled with arylboronic acids and potassium aryltrifluoroborates using only 0.5 mol% of oxime palladacycles 1 under aqueous conditions at 110 °C. Under these simple phosphane-free reaction conditions a wide array of biaryl derivatives has been prepared in high yields. This methodology allows in situ phenol sulfonation and one-pot Suzuki arylation as well as the employment of microwave irradiation conditions.
Imidazolylsulfonates: Electrophilic partners in cross-coupling reactions
Albaneze-Walker, Jennifer,Raju, Ravinder,Vance, Jennifer A.,Goodman, Andrew J.,Reeder, Michael R.,Liao, Jing,Maust, Mathew T.,Irish, Patrick A.,Espino, Peter,Andrews, David R.
supporting information; experimental part, p. 1463 - 1466 (2009/08/07)
Aryl imidazolylsulfonates participate as electrophilic coupling partners in palladium-mediated cross-coupling reactions. The aryl imidazolylsulfonates display good stability while maintaining good reactivity in a variety of palladium-catalyzed coupling reactions. Imidazolylsulfonates are a practical and economic alternative to triflates.
