Efficient Access to 1,4-Benzothiazine: Palladium-Catalyzed Double C–S Bond Formation Using Na2S2O3 as Sulfurating Reagent

Qiao, Zongjun; Liu, Hui; Xiao, Xiao; Fu, Yana; Wei, Jianpeng; Li, Yuxue; Jiang, Xuefeng

doi:10.1021/ol400618k

Cited by 169 publications

(48 citation statements)

References 50 publications

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“…In 2013, Jiang and co-workers developed a Pd-catalyzed double carbon-sulfur bond formation using sodium thiosulfate as sulfurating reagent [29] (Fig. 19a).…”

Section: Synthesis Of Thioethersmentioning

confidence: 99%

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Feng¹,

Tang²,

Liang³

et al. 2016

CTMC

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1,501

641

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The impact of the development of sulfur therapeutics is instrumental to the evolution of the pharmaceutical industry. Sulfur-derived functional groups can be found in a broad range of pharmaceuticals and natural products. For centuries, sulfur continues to maintain its status as the dominating heteroatom integrated into a set of 362 sulfur-containing FDA approved drugs (besides oxygen or nitrogen) through the present. Sulfonamides, thioethers, sulfones and Penicillin are the most common scaffolds in sulfur containing drugs, which are well studied both on synthesis and application during the past decades. In this review, these four moieties in pharmaceuticals and recent advances in the synthesis of the corresponding core scaffolds are presented.

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“…In 2013, Jiang and co-workers developed a Pd-catalyzed double carbon-sulfur bond formation using sodium thiosulfate as sulfurating reagent [29] (Fig. 19a).…”

Section: Synthesis Of Thioethersmentioning

confidence: 99%

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Feng¹,

Tang²,

Liang³

et al. 2016

CTMC

Self Cite

1,501

641

View full text Add to dashboard Cite

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“…The resulting 4benzothiazine derivatives are suitable precursors for various pharmaceutically active compounds and natural products (Scheme 13). [27]…”

Section: Palladiummentioning

confidence: 99%

Transition‐Metal‐Catalyzed CS Bond Coupling Reaction

Lee

Liu

Badsara

2014

Chemistry An Asian Journal

437

122

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Sulfur-containing molecules such as thioethers are commonly found in chemical biology, organic synthesis, and materials chemistry. While many reliable methods have been developed for preparing these compounds, harsh reaction conditions are usually required in the traditional methods. The transition metals have been applied in this field, and the palladium-catalyzed coupling of thiols with aryl halides and pseudo halides is one of the most important methods in the synthesis of thioethers. Other metals have also been used for the same purpose. Here, we summarize recent efforts in metal-catalyzed C-S bond cross-coupling reactions, focusing especially on the coupling of thiols with aryl- and vinyl halides based on different metals.

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“…Through a similar strategy, Zhou’s group achieved the construction of such compounds employing KSCN instead of KSAc 37 . Ma’s group 38 and Jiang’s group 39 have reported the synthesis of aryl and alkyl sulfides with sulfur powder and Na 2 S 2 O 3 as sulfuration agents, respectively. In addition, methods for the formation of C–S bonds involving electrophilic benzenesulfonothioates were also explored (Fig.…”

Section: Introductionmentioning

confidence: 99%

Nickel-catalyzed reductive thiolation and selenylation of unactivated alkyl bromides

et al. 2018

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Chalcogen-containing compounds have received considerable attention because of their manifold applications in agrochemicals, pharmaceuticals, and material science. While many classical methods have been developed for preparing organic sulfides, most of them exploited the transition-metal-catalyzed cross-couplings of aryl halides or pseudo halides with thiols or disulfides, with harsh reaction conditions usually being required. Herein, we present a user-friendly, nickel-catalyzed reductive thiolation of unactivated primary and secondary alkyl bromides with thiosulfonates as reliable thiolation reagents, which are easily prepared and bench-stable. Furthermore, a series of selenides is also prepared in a similar fashion with selenosulfonates as selenolation reagents. This catalytic method offers a facile synthesis of a wide range of unsymmetrical alkyl-aryl or alkyl-alkyl sulfides and selenides under mild conditions with an excellent tolerance of functional groups. Likewise, the use of sensitive and stoichiometric organometallic reagents can be avoided.

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Efficient Access to 1,4-Benzothiazine: Palladium-Catalyzed Double C–S Bond Formation Using Na₂S₂O₃ as Sulfurating Reagent

Cited by 169 publications

References 50 publications

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Transition‐Metal‐Catalyzed CS Bond Coupling Reaction

Nickel-catalyzed reductive thiolation and selenylation of unactivated alkyl bromides

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