LiBr-Catalyzed C3-Disulfuration between Indole and <i>N</i>-Dithiophthalimide

Wang, Dungai; Li, Wangyu; Shi, Keqiang; Pan, Yuanjiang

doi:10.1021/acs.joc.1c02556

Cited by 10 publications

(8 citation statements)

References 37 publications

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“…Very recently, Pan and coworkers developed a simple and green LiBr‐catalyzed protocol for the C3‐disulfuration of indole derivatives 38 with N ‐dithiophthalimides ( 12 , Harpp reagents) under ambient conditions (Scheme 14). [110] The reaction does not require transition metal catalysts and strong bases but employs cost‐effective LiBr as the sole catalyst. The protocol exhibited a broad substrate scope, allowing the transformations across a vast range of N−H/N−Me/N−Bn indoles and aryl, benzyl, primary/secondary/tertiary alkyl Harpp reagents.…”

Section: C−h Disulfurationmentioning

confidence: 99%

Direct C−H Sulfuration: Synthesis of Disulfides, Dithiocarbamates, Xanthates, Thiocarbamates and Thiocarbonates

Sun,

Xu,

Yang

et al. 2024

Chemistry An Asian Journal

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In light of the important biological activities and widespread applications of organic disulfides, dithiocarbamates, xanthates, thiocarbamates and thiocarbonates, the continual persuit of efficient methods for their synthesis remains crucial. Traditionally, the preparation of such compounds heavily relied on intricate multi‐step syntheses and the use of highly prefunctionalized starting materials. Over the past two decades, the direct sulfuration of C–H bonds has evolved into a straightforward, atom‐ and step‐economical method for the preparation of organosulfur compounds. This review aims to provide an up‐to‐date discussion on direct C–H disulfuration, dithiocarbamation, xanthylation, thiocarbamation and thiocarbonation, with a special focus on describing scopes and mechanistic aspects. Moreover, the synthetic limitations and applications of some of these methodologies, along with the key unsolved challenges to be addressed in the future are also discussed. The majority of examples covered in this review are accomplished via metal‐free, photochemical or electrochemical approaches, which are in alignment with the overraching objectives of green and sustainable chemistry. This comprehensive review aims to consolidate recent advancements, providing valuable insights into the dynamic landscape of efficient and sustainable synthetic strategies for these crucial classes of organosulfur compounds.

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Section: C−h Disulfurationmentioning

confidence: 99%

Direct C−H Sulfuration: Synthesis of Disulfides, Dithiocarbamates, Xanthates, Thiocarbamates and Thiocarbonates

Sun,

Xu,

Yang

et al. 2024

Chemistry An Asian Journal

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“…However, most of the literature reported that the reaction was carried out using thiol as a substrate, with a bad smell and low commercial value . Thus, considerable efforts had been spent to develop alternative reagents as S-S sources to synthesize disulfides, for example, RSSSSR, RSSLG, NuSSNu, RSSAc, and RSSTs (Scheme b).…”

Section: Introductionmentioning

confidence: 99%

Photocatalytic C–H Disulfuration for the Preparation of Indolizine-3-disulfides

Wan

et al. 2022

J. Org. Chem.

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A photocatalytic C−H disulfuration of indolizines was developed, giving an approach to a wide variety of indolizine-3-disulfides with good yields. Trisulfide dioxides were explored as a high-efficient disulfuration reagent. This disulfuration reaction could be scaled up to grams. Mechanistic studies support a photoinduced pathway involving the generation of indolizine cationic radicals. A bulky alkyl substituent on terminal sulfur of trisulfide dioxide A was necessary for selective formation of disulfide over monosulfide.

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“…Since the synthesis of the Harpp reagents in 1971, it has found widespread application as an electrophilic reagent in the total synthesis of natural products . In recent years, researchers have explored new avenues for the use of the Harpp reagents . In 2019, the Wang group developed a copper-catalyzed coupling reaction between the Harpp reagent and phenylboronic acid.…”

mentioning

confidence: 99%