Journal ArticleDOI
Iron‐Induced Regio‐ and Stereoselective Addition of Sulfenyl Chlorides to Alkynes by a Radical Pathway
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TLDR
The radical addition of the Cl-S σ-bond in sulfenyl chlorides to various C-C triple bonds has been achieved with excellent regio- and stereoselectivity in the presence of a catalytic amount of a common iron salt.Abstract:
The radical addition of the ClS σ-bond in sulfenyl chlorides to various CC triple bonds has been achieved with excellent regio- and stereoselectivity in the presence of a catalytic amount of a common iron salt. The reaction is compatible with a variety of functional groups and can be scaled up to the gram-scale with no loss in yield. As well as terminal alkynes, internal alkynes underwent stereodefined chlorothiolation to provide tetrasubstituted alkynes. Preliminary mechanistic investigations revealed a plausible radical process involving a sulfur-centered radical intermediate via iron-mediated homolysis of the ClS bond. The resulting chlorothiolation adducts can be readily transformed to the structurally complex alkenyl sulfides by cross-coupling reactions. The present reaction can also be applied to the complementary synthesis of the potentially useful bis-sulfoxide ligands for transition-metal-catalyzed reactions.read more
Citations
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Recent advances in radical transformations of internal alkynes
TL;DR: This review highlights the recent progress in this rapidly growing area by presenting a series of catalytic oxidative reactions, mechanisms and applications which have appeared in the most recent literature.
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Recent advances in sulfur- and phosphorous-centered radical reactions for the formation of S–C and P–C bonds
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Nickel-catalyzed direct thiolation of C(sp(3))-H bonds in aliphatic amides
Xie Wang,Renhua Qiu,Renhua Qiu,Yan Chunyang,Vutukuri Prakash Reddy,Longzhi Zhu,Xinhua Xu,Shuang-Feng Yin +7 more
TL;DR: Nickel-catalyzed thiolation of the inactivated methyl C(sp(3))-H bonds of aliphatic amides with disulfide is described, which is a novel strategy for the synthesis of thioethers with the ultimate goal of generatingThioether carboxylic acids with various functional groups.
Journal ArticleDOI
Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes.
TL;DR: The silver‐catalyzed intermolecular aminosulfonylation of terminal alkynes with sodium sulfinates and TMSN3 enables the stereoselective synthesis of a wide range of β‐sulfonyl enamines without electron‐withdrawing groups on the nitrogen atom.
Journal ArticleDOI
A Reaction of Triazoles with Thioesters to Produce β‐Sulfanyl Enamides by Insertion of an Enamine Moiety into the Sulfur–Carbonyl Bond
TL;DR: N-Sulfonyl-1,2,3-triazoles react with thioesters in the presence of a rhodium(II) catalyst to produce β-sulfanyl enamides in a stereoselective manner, leading to the formation of sulfur-containing lactams.
References
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Palladium-Catalyzed Suzuki-Miyaura Cross-coupling Reactions Employing Dialkylbiaryl Phosphine Ligands
Ruben Martin,Stephen L. Buchwald +1 more
TL;DR: An overview of the use and impact of dialkylbiarylphosphine ligands in the Suzuki-Miyaura cross-coupling reaction and the utility of these ligands has been successfully demonstrated in a wide number of synthetic applications, including industrially relevant processes.
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Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions
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Electron spin resonance studies of transient alkyl radicals
TL;DR: In this article, the ESR lines are found to be narrow; considerable fine structure is observable, permitting positive assignment of the radical species, and accurate hyperfine constants are reported for 21 alkyl and cycloalkyl radicals, including several deuterated species.
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Chiral sulfur ligands for asymmetric catalysis.
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Radical Cascades Initiated by Intermolecular Radical Addition to Alkynes and Related Triple Bond Systems
TL;DR: In this paper, the authors studied the effect of intermolecular radical cyclizations and multicomponent radical cascades in solution, which are initiated by intermolescular radical addition to C-C triple bond in alkynes as well as to related C?N triple bonds in nitriles and isonitriles, arranged according to the atom that carries the unpaired electron in the attacking radical and cover main group IV-VI elements.
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