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Amine-borane complex-initiated SF₅Cl radical addition on alkenes and alkynes.

ABSTRACT: The SF₅Cl radical addition on unsaturated compounds was performed using an air-stable amine-borane complex as the radical initiator. This method showed to be complementary to the classic Et₃B-mediated SF₅Cl addition on alkenes and alkynes. A total of seven alkene and three alkyne derivatives were tested in the reaction, with yields ranging from 3% to 85%.

SUBMITTER: Gilbert A

PROVIDER: S-EPMC7753108 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Amine-borane complex-initiated SF5Cl radical addition on alkenes and alkynes.

Gilbert Audrey A Langowski Pauline P Delgado Marine M Chabaud Laurent L Pucheault Mathieu M Paquin Jean-François JF

Beilstein journal of organic chemistry 20201216

The SF5Cl radical addition on unsaturated compounds was performed using an air-stable amine-borane complex as the radical initiator. This method showed to be complementary to the classic Et3B-mediated SF5Cl addition on alkenes and alkynes. A total of seven alkene and three alkyne derivatives were tested in the reaction, with yields ranging from 3% to 85%. ...[more]

PMID: 33414854

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Correction: Amine-borane complex-initiated SF5Cl radical addition on alkenes and alkynes.

Project description:[This corrects the article DOI: 10.3762/bjoc.16.256.].

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Project description:Fluorinated or fluoroalkylated alcohols are common structural motifs in biologically active molecules, natural products, and pharmaceuticals. However, pentafluorosulfanyl (SF5) alcohols, a unique class of SF5 compounds that serve as synthetically valuable building blocks, are difficult to prepare with current methodologies. In this article, we present a single-step, metal-free, and photo-induced hydroxypentafluorosulfanylation of styrenes or α,β-unsaturated esters/amide, producing a series of structurally diverse pentafluorosulfanyl alcohols with up to 89% yields. This reaction is mild and operationally simple, using molecular oxygen as the hydroxy source. The protocol is suitable for a wide range of alkenes, including natural products and drug molecule derivatives. The formed SF5 alcohol units can be readily converted into diverse functionalized SF5 compounds, such as α-SF5 ketones, SF5 diols, and SF5 cyclic carbonates. The potential applications of these SF5 compounds in pharmaceutical and material sciences are vast, making this research a step forward in the field.

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