TY - JOUR AU - Dagenais, Robin; Lauriers, Antoine Jobin-Des; Legault, Claude Y. TI - Iodine(III)-Mediated Oxidative Hydrolysis of Haloalkenes: Investigation of the Effect of Iodine(III) Reagents SN - 0039-7881 SN - 1437-210X PY - 2017 JO - Synthesis JF - Synthesis LA - EN VL - 49 IS - 13 SP - 2928 EP - 2932 ET - 2017/06/07 DA - 2017/06/20 KW - hypervalence KW - iodine KW - oxidation KW - vinyl halides KW - chemoselectivity AB - The iodine(III)-mediated oxidative transposition of vinyl halides to the corresponding α-halo ketones has been recently reported. The method is high yielding and offers good substrate scope. The investigation of other iodine(III) reagents to promote this reaction is described. The newly developed protocol reduces the number of waste products formed in the synthetic transformation. A structure–reactivity relationship study of numerous [hydroxy(tosyloxy)iodo]arenes toward haloalkenes is reported. The results highlight the challenge of obtaining a chemoselective reaction using these reagents. PB - © Georg Thieme Verlag DO - 10.1055/s-0036-1588439 UR - http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0036-1588439 ER -