2020
DOI: 10.1021/acs.orglett.0c02341
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Electrochemically Enabled Sulfonylation of Alkynes with Sodium Sulfinates

Abstract: An electrochemical sulfonylation of alkynes with sodium sulfinates was achieved for the first time at room temperature. Employing this electrolysis strategy, the reaction occurs efficiently under transition-metal-free, external oxidant-free, and base-free conditions and furnishes diverse alkynyl sulfones in satisfactory yield with broad functional group tolerance.

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Cited by 39 publications
(54 citation statements)
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References 52 publications
(23 reference statements)
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“…However, reasonable yields can be obtained via carefully controlled condensation reactions between propiolates and amines. , Additionally, there are other methods that afford propiolamides such as acylation reactions employing carbamoyl chlorides, ,, photocatalyzed decarboxylative ynonylation, dehydrogenative coupling of terminal alkynes with formamides, or palladium-catalyzed multicomponent reactions among alkynes, isonitriles, and carboxylates . More esoteric electron deficient alkynes such as ethynylsulfones are conveniently isolated from sulfonyl chlorides, , sulfonyl hydrazides, sulfinates, , or via multicomponent reactions, for example, photocatalyzed coupling of sulfur dioxide and alkynyl bromides. , While their use as a substrate in Michael reactions is comparatively rare next to other activated alkynes, they are still very reactive in reported examples , and this provides ample opportunity for further work. Propiolonitriles are also susceptible to 1,4-conjugate additions from heteronucleophiles, however, they are not as common in this context due to a lack of functional modularity.…”
Section: Introductionmentioning
confidence: 99%
“…However, reasonable yields can be obtained via carefully controlled condensation reactions between propiolates and amines. , Additionally, there are other methods that afford propiolamides such as acylation reactions employing carbamoyl chlorides, ,, photocatalyzed decarboxylative ynonylation, dehydrogenative coupling of terminal alkynes with formamides, or palladium-catalyzed multicomponent reactions among alkynes, isonitriles, and carboxylates . More esoteric electron deficient alkynes such as ethynylsulfones are conveniently isolated from sulfonyl chlorides, , sulfonyl hydrazides, sulfinates, , or via multicomponent reactions, for example, photocatalyzed coupling of sulfur dioxide and alkynyl bromides. , While their use as a substrate in Michael reactions is comparatively rare next to other activated alkynes, they are still very reactive in reported examples , and this provides ample opportunity for further work. Propiolonitriles are also susceptible to 1,4-conjugate additions from heteronucleophiles, however, they are not as common in this context due to a lack of functional modularity.…”
Section: Introductionmentioning
confidence: 99%
“…Alkynyl sulfones which showed excellent bioactivity in various fields could be obtained by the sulfonylation of alkynes. , In 2019, Tang and co-workers reported a sulfonylation of alkynes using sulfonyl hydrazides ( 139 ) and terminal alkynes ( 140 ) as substrates (Scheme ). The substrates reacted in an undivided cell equipped with a RVC anode (100 PPI, 1 cm × 1 cm × 1.2 cm) and a Pt plate cathode (1 cm × 1 cm) with a constant potential of 1.2 V (vs Ag/AgCl) under an O 2 atmosphere, TBAI was selected as an electrolyte, and K 2 CO 3 was used as an additive.…”
Section: Sulfonylation Of Alkenes and Alkynesmentioning
confidence: 99%
“…HRMS data were recorded on ThermoFisher LTQ Orbitrap XL or Agilent 6500QTOFMS-ESI. All 1 H NMR, 13 C NMR spectra were recorded on Bruker DRX-600 and AMX-400 instruments. Chemical shifts were given in parts per million (ppm, δ), referenced to the solvent peak of CDCl3, defined at δ = 7.26 ( 1 H NMR), defined at δ = 77.16 ( 13 C NMR).…”
Section: Accepted Manuscriptmentioning
confidence: 99%
“…10 In particular, electrosynthesis provides an environmentally friendly tool for the generation of sulfonyl radicals from sulfonyl compounds including sulfonyl chlorides, sulfonyl hydrazides, sulfinic acids, and sodium sulfinates. 11 Building on these prior work [11][12] and our recent investigations on electrochemical sulfonylation of alkynes 13 and electrochemical transformation of o-alkynylanilines, 14 we here present an electrochemical annulation of o-alkynylanilines with sodium sulfinates to construct 3-sulfonylindoles at room temperature. The current protocol exhibits good functional group compatibility with a range of substrates under mild conditions, which avoids the use of transition metals, chemical oxidants, and potentially explosive substrates.…”
mentioning
confidence: 99%