2020
DOI: 10.1021/acs.orglett.0c02067
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Cine-Substitutions at Five-Membered Hetarenes Enabled by Sulfonium Salts

Abstract: We report a nucleophilic substitution reaction of five-membered hetarylsulfonium salts that results in a change of the substitution pattern on the arene. The products of these cine -substitutions are hard to access synthetically otherwise. The sulfonium salts that serve as starting materials are generated by a highly site-selective C–H functionalization reaction.

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Cited by 35 publications
(26 citation statements)
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“…In 2020, the Ritter group reported a cine -substitution of electron-rich heteroarylsulfonium salts where various N -containing heterocycles were used as N -nucleophiles. 30 This cine -substitution goes through a novel reaction pathway elucidated in Scheme 22 , that is, the sulfur ylide is formed after addition of the nucleophile to the heteroarylsulfonium salt, followed by the protonation and elimination to give the final product. It should be noted that in this chemistry, the sulfonium group showed distinguished leaving ability from other (pseudo)halides.…”
Section: Thianthrenation-enabled Site-selective Functionalization Of ...mentioning
confidence: 99%
“…In 2020, the Ritter group reported a cine -substitution of electron-rich heteroarylsulfonium salts where various N -containing heterocycles were used as N -nucleophiles. 30 This cine -substitution goes through a novel reaction pathway elucidated in Scheme 22 , that is, the sulfur ylide is formed after addition of the nucleophile to the heteroarylsulfonium salt, followed by the protonation and elimination to give the final product. It should be noted that in this chemistry, the sulfonium group showed distinguished leaving ability from other (pseudo)halides.…”
Section: Thianthrenation-enabled Site-selective Functionalization Of ...mentioning
confidence: 99%
“…The combination of cine substitution with site-selective C-H functionalization allows the synthesis of arenes with unusual substitution patterns, which are hard to access otherwise (Scheme 11). 22 Scheme 11 Cine substitution of heterocyclic sulfonium salts 22…”
Section: Cine Substitutionmentioning
confidence: 99%
“…Recently, sulfonium salts have been attracting increasing attention due to their broad applications in carbon-carbon and carbon-heteroatom bond formation reactions, [22][23][24][25][26][27][28][29][30][31][32][33][34] especially for the construction of C-N bonds. In 2019, the Ritter group reported the first C(sp 2 )-N cross-coupling reaction of aryl thianthrenium salts (Scheme 1a, top).…”
Section: Introductionmentioning
confidence: 99%