2015
DOI: 10.1021/acs.orglett.5b01540
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Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate

Abstract: A method for the preparation of aryl and heteroaryl sulfonamides using 2,4,6-trichlorophenyl chlorosulfate (TCPC) is described. The reaction of 2-pyridylzinc reagents with TCPC resulted in 2,4,6-trichlorophenyl (TCP) pyridine-2-sulfonates, and the parent pyridine-2-sulfonate was shown to react with amines. Less electron-rich aryl- and heteroarylzinc reagents reacted with TCPC to afford sulfonyl chlorides that were converted in situ to sulfonamides.

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Cited by 10 publications
(4 citation statements)
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“…The transformation of sulfonate, proceeded by breaking the S–O bond, was mainly carried out via a sulfonyl transfer mechanism. For example, sulfonates could react with aryl Grignard reagent to form sulfones, and activated sulfonates could combine with amines to produce sulfonamide . However, transition-metal-catalyzed transformation of sulfonates via S–O bond cleavage remains very rare.…”
mentioning
confidence: 92%
See 1 more Smart Citation
“…The transformation of sulfonate, proceeded by breaking the S–O bond, was mainly carried out via a sulfonyl transfer mechanism. For example, sulfonates could react with aryl Grignard reagent to form sulfones, and activated sulfonates could combine with amines to produce sulfonamide . However, transition-metal-catalyzed transformation of sulfonates via S–O bond cleavage remains very rare.…”
mentioning
confidence: 92%
“…For example, sulfonates could react with aryl Grignard reagent to form sulfones, 14 and activated sulfonates could combine with amines to produce sulfonamide. 15 However, transitionmetal-catalyzed transformation of sulfonates via S−O bond cleavage remains very rare. The Buchwald group discovered a palladium-catalyzed chlorosulfonylation of arylboronic acids to synthesize aryl sulfonamides, in which the palladium catalyst could selectively be oxidatively added into the S−O bond 16 (Scheme 1c).…”
mentioning
confidence: 99%
“… In addition, free α-branched benzyl sulfonic acids are sensitive and gradually decompose upon storage . Activations for the reaction with amines by the use of milder leaving groups such as electron-deficient phenolates or in situ activation with Ph 3 PO/(TfO) 2 also failed, and rearrangement to the corresponding olefinic sulfonamide was observed.…”
Section: Introductionmentioning
confidence: 99%
“…[1] They are also important structural motifs in drugs such as Almotriptan, [2] Avitriptan [3] and Sumatriptan [4] (Figure 1). Previous methods to access sulfonamides range from simple N–S bond formation, [5] to tandem reactions that also include S=O, [6] C–S, [7] and C–N bond-forming reactions. [8] Although α-arylation of unfunctionalized methyl sulfonamides with aryl halides to form C–C bonds is an attractive route to these important compounds, such transformations have met with limited success.…”
Section: Introductionmentioning
confidence: 99%