Abstract
AbstractBy visible‐light photoredox catalysis with copper complexes, sulfoximidoyl chlorides add to terminal aryl alkynes to give the corresponding (E)‐β‐chlorovinyl sulfoximines with exclusive regio‐ and stereoselectivities in high yields. Two representative products have been characterized by X‐ray crystal structure analysis. Radicals appear to be decisive intermediates. As demonstrated by two subsequent reactions, the products can be derivatized.magnified image
Highlights
In each of the aforementioned examples, sulfonyl radicals A have been proposed to be key intermediates
Analogous addition reactions of sulfoximidoyl chlorides 4 to alkynes 2 are of interest as they should lead to substituted vinyl sulfoximines 5 with numerous potential applications in organic synthesis.[9,10]
In light of the very impressive advances in visiblelight photoredox catalysis with copper complexes,[11] we decided to focus on studying the potential of such systems
Summary
Scheme 1. (Top) previous work utilizing sulfonyl radicals A; (bottom) envisaged reactions via sulfoximidoyl radical B and discovered transformation described here. (Top) previous work utilizing sulfonyl radicals A; (bottom) envisaged reactions via sulfoximidoyl radical B and discovered transformation described here. To our delight, both compounds reacted when irradiated in THF for 8 h at room temperature with blue LED light in the presence of copper(II) chloride (10 mol %) and dtbpy (dtbpy = 4,4’-di-tert-butyl-2-2’-bipyridine, 20 mol %) providing addition product 5 a in 10% yield (Table 1, entry 1)
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