SES sulfinate was made from vinyltrimethylsilane according to a modified literature procedure (See Supporting Information). All reactions proceeded in high yield. PMB-R, oNB-R, and SES sulfinates coupled with aryl iodides in high yields at 50 °C in the presence of CuI/HMNPC (Figure ). In contrast, SMOPS, TBS-R, and Rongacyl sulfinate resulted in either low yields or no product. It is worth noting that higher yields for the coupling of TBS-R sulfinate were obtainable when the aryl iodide was held in excess (3 equiv) as per the original literature report. Only SES sulfinate coupled with aryl bromides albeit at elevated (100 °C) temperatures.