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Updated: Jan 18, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

B(C₆F₅)₃触媒によるアミノアルケン類の分子内チオアミノ化およびセレノアミノ化

Kanta Pajujantaro¹, Changjiang Wu¹, Haifan Wang¹

¹Organoselenium Synthesis and Function Laboratory, School of Pharmacy, Nantong University, Nantong 226019, People's Republic of China.

The Journal of organic chemistry

|January 15, 2026

Abstract:

A metal-free borane-catalyzed chalcogenative cyclization strategy for constructing chalcogen-containing heterocycles from unactivated alkenes with thiosuccinimides or selenophthalimide is developed herein. This method results in excellent substrate and functional group tolerance and high levels of chemo- and regioselectivity. Furthermore, the protocol enables the late-stage diversification of commercially available pharmaceuticals. Mechanistic studies suggest that the borane catalyst activates thiosuccinimides and selenophthalimides to form electrophilic species, which subsequently induce this chalcogenative annulation.

キーワード:

金属フリー触媒ボラン触媒チオアミノ化セレノアミノ化複素環合成医薬品化学

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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

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Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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Amines to Alkenes: Hofmann Elimination

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Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
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Radical Substitution: Allylic Bromination

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