Synthesis of Sulfones from Organozinc Reagents, DABSO, and Alkyl Halides

Rocke, Benjamin N.; Bahnck, Kevin B.; Herr, Michael; Lavergne, Sophie Y.; Mascitti, Vincent; Perreault, Christian; Polívková, Jana; Shavnya, Andrei

doi:10.1021/ol4031233

Cited by 151 publications

(44 citation statements)

References 38 publications

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“…Rocke and co-workers reported that organozinc reagents reacted with DABSO and the resulting zinc sulfinate salts were alkylated in situ to afford sulfones [38]. This transformation has a broad scope and is compatible with a wide range of functional groups including nitrile, secondary carbamates, and nitrogen-containing heterocycles (Fig.…”

Section: Synthesis Of Sulfonesmentioning

confidence: 99%

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

Feng¹,

Tang²,

Liang³

et al. 2016

CTMC

1,431

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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Section: Synthesis Of Sulfonesmentioning

confidence: 99%

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

Feng¹,

Tang²,

Liang³

et al. 2016

CTMC

1,431

641

View full text Add to dashboard Cite

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“…792187) was invented (Figure 1D). PSMS ( 6 ) can be synthesized in one step from bromomethyl phenyl sulfone ( 5 ) 11 and is a free-flowing, bench-stable (stable at room temperature under air over 4 months), white powder whose structure was characterized by X-ray crystallography as the hexahydrate. PSMS ( 6 ) enables the installation of a (phenylsulfonyl)methyl group onto a heteroarene at both an early and late stage of the synthesis.…”

mentioning

confidence: 99%

C–H Methylation of Heteroarenes Inspired by Radical SAM Methyl Transferase

et al. 2014

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A practical C–H functionalization method for the methylation of heteroarenes is presented. Inspiration from Nature’s methylating agent, S-adenosylmethionine (SAM), allowed for the design and development of zinc bis(phenylsulfonylmethanesulfinate), or PSMS. The action of PSMS on a heteroarene generates a (phenylsulfonyl)methylated intermediate that can be easily separated from unreacted starting material. This intermediate can then be desulfonylated to the methylated product or elaborated to a deuteriomethylated product, and can divergently access medicinally important motifs. This mild, operationally simple protocol that can be conducted in open air at room temperature is compatible with sensitive functional groups for the late-stage functionalization of pharmacologically relevant substrates.

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“…For example, in situ treatment of the sulfinate with an alkyl bromide delivers alkylaryl sulfone products ( 6a–e ). 25 The use of epoxides as the electrophiles provides β-hydroxy sulfones ( 6f–j ). 25 b Treatment with in situ generated chloroamines provides sulfonamides ( 6k–o ), 26 and treatment with NFSI, which is a source of electrophilic fluorine, generates the corresponding sulfonyl fluorides ( 6p–t ).…”

Section: Resultsmentioning

confidence: 99%