Jia Tiezheng, Zhang Mengnan, Sagamanova Irina K, Wang Carol Y, Walsh Patrick J
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
Org Lett. 2015 Mar 6;17(5):1168-71. doi: 10.1021/acs.orglett.5b00092. Epub 2015 Feb 16.
Diaryl sulfoxides are synthesized from aryl benzyl sulfoxides and aryl chlorides via three sequential catalytic cycles all promoted by a NiXantPhos-based palladium catalyst. The key step is S-arylation of a sulfenate anion. An air- and moisture-stable precatalyst derived from NiXantPhos efficiently facilitates the transformation. Various functional groups, including those with acidic protons, were tolerated. This method can also be extended to methyl and dibenzyl sulfoxides substrates.
二芳基亚砜是通过基于NiXantPhos的钯催化剂促进的三个连续催化循环,由芳基苄基亚砜和芳基氯化物合成的。关键步骤是亚磺酸根阴离子的S-芳基化。由NiXantPhos衍生的一种对空气和湿气稳定的预催化剂有效地促进了这种转化。各种官能团,包括那些带有酸性质子的官能团,都能耐受。该方法还可以扩展到甲基和二苄基亚砜底物。