2023
DOI: 10.26434/chemrxiv-2023-t0d4n
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Strain-Enabled S-Arylation and S-Alkenylation of Sulfinamides

Abstract: Converting commercially available and affordable chiral sulfinamides to pharmaceutically important chiral sulfoximines via SIV-functionalization is synthetically appealing, however, remains little developed due to the competing N-functionalization pathway. To address this challenge, we disclose a strain-enabled stereospecific and chemoselective S-arylation and S-alkenylation of sulfinamides using arynes and cyclic alkynes. The origin of high SIV-selectivity is elucidated by density functional theory (DFT) calc… Show more

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Cited by 5 publications
(7 citation statements)
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“…One challenge in preparing intermediates 5d and 5h was the compatibility of the aniline group during sulfoximine synthesis. A “–NHBoc” motif could hardly be tolerated in previous S-arylation methods using the hypervalent iodine reagent or aryne precursor. , However, aryl boronic acid bearing a para “–NHBoc” motif was commercially available and could be directly converted to the corresponding sulfoximines in satisfactory yield using our method ( 5a , 5e ). Following the conventional N- modification and deprotection, , the target intermediates were obtained in four steps.…”
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confidence: 92%
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“…One challenge in preparing intermediates 5d and 5h was the compatibility of the aniline group during sulfoximine synthesis. A “–NHBoc” motif could hardly be tolerated in previous S-arylation methods using the hypervalent iodine reagent or aryne precursor. , However, aryl boronic acid bearing a para “–NHBoc” motif was commercially available and could be directly converted to the corresponding sulfoximines in satisfactory yield using our method ( 5a , 5e ). Following the conventional N- modification and deprotection, , the target intermediates were obtained in four steps.…”
mentioning
confidence: 92%
“…For the preparation of aryl sulfoximines, a copper-catalyzed S-arylation of sulfinamides using hypervalent iodine reagents has been developed (Figure A) . We have also discovered a novel metal-free S-arylation and alkenylation reaction enabled by strain-containing molecules (Figure B) . These two methods successfully addressed the challenge of S/N chemoselectivity using different strategies.…”
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confidence: 99%
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“…Exogenous free radical inhibitors are not synthesized by the human body and must be obtained from external sources, primarily from natural products (NPs) such as vitamins [13], polyphenols, and flavonoids [14]. Some exogenous free radical inhibitors, such as tert-butyl hydroquinone, are artificially synthesized [15]. NPs have long been considered promising exogenous antioxidant candidates [16].…”
Section: Introductionmentioning
confidence: 99%
“…The total number of intensive care unit beds was 181,000, equating to 12.8 beds per 100,000 individuals. [7] Moreover, the combined expertise and skill of experts and medical staff have been used to coordinate a better response to the current epidemic. Government authorities have approved 13 vaccine candidates for emergency use, including 5 inactivated vaccines, 5 recombinant protein vaccines, and 3 vector-based vaccines.…”
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confidence: 99%