@article {48001,
	title = {Solvent-driven mono- and bis-sulfenylation of (E)-beta-iodovinyl sulfones with thiols for flexible synthesis of 1,2-thiosulfonylalkenes and 1,2-dithioalkenes},
	journal = {Journal of Organic Chemistry},
	volume = {87},
	year = {2022},
	month = {MAR},
	pages = {3934-3951},
	type = {Article},
	abstract = {<p>
	The nature of solvent is a key factor for stereoselective mono-and bis-thiolation of (E)-beta-iodovinyl sulfones with thiols under basic conditions. A novel and unprecedented vicinal bisthiolation of (E)-beta-iodovinyl sulfones with thiols under the influence of K2CO3/DMSO at room temperature for quick assembly of (E)-1,2-dithio-1-alkenes is presented. Solvent-induced stereoselective monosulfenylation of (E)-beta-iodovinyl sulfones with thiols has also been established for the synthesis of both (E)- and (Z)-1,2-thiosulfonylethenes in MeCN and MeOH, respectively. Moreover, K2CO3-mediated desulfonylative-sulfenylation of (Z)-1,2-thiosulfonylethenes with thiols in DMSO furnished unsymmetrical (Z)-1,2-dithio-1-alkenes for the first time. The solvent-dependent versatile reactivity of (E)-beta-iodovinyl sulfones has been successfully explored to provide a set of (E)-/(Z)-1,2-dithio-1-alkenes and (E)-/(Z)-1,2-thiosulfonyl-1-alkenes in good to high yields with excellent stereoselectivities. Notably, this operationally simple process utilizes a broad substrate scope with good functional group tolerance and compatibility. The efficacy of the process has been proven for gram-scale reactions, and plausible mechanistic models are outlined on the basis of experimental results and control experiments.</p>
},
	issn = {0022-3263},
	doi = {10.1021/acs.joc.1c02444},
	author = {Reddy, Raju Jannapu and Kumari, Arram Haritha and Sharadha, Nunavath and Krishna, Gamidi Rama}
}
