A newly developed aqueous system with acid and phosphide was introduced in which odorless and stable sodium arylsulfinates can in situ generate arylsulfenyl radicals. These radicals have high reactivity to react with alkynes, alkenes, and H-phosphine oxides for the synthesis of alkyl and alkenyl sulfides and phosphonothioates. The control experiments and quantum calculations are also performed to gain insights into the generation mechanism of arylsulfenyl radicals. Notably, the chemistry is free of thiol odors, organic solvents, and metals.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.6b02459DOI Listing

Publication Analysis

Top Keywords

alkyl alkenyl
8
alkenyl sulfides
8
sulfides phosphonothioates
8
sodium arylsulfinates
8
arylsulfenyl radicals
8
acid/phosphide-induced radical
4
radical route
4
route alkyl
4
phosphonothioates sodium
4
arylsulfinates water
4

Similar Publications

A site-selective coupling involving quinoxalin-2-ones with alkenes and alkynes has been developed through synergistic visible-light photoredox cobalt catalysis. This method enables C3-selective alkylation and alkenylation of both -substituted and -unsubstituted quinoxalin-2-ones, achieving high yields under mild conditions. Of note, the protocol facilitates the incorporation of two alkene units, leading to a formal three-component coupling, whereas a two-component coupling is preferred for alkynes.

View Article and Find Full Text PDF

We present a highly efficient and versatile nickel-catalyzed protocol for the reductive cross-coupling of unactivated CFH-substituted electrophiles with a wide variety of aryl and alkenyl halides. This novel approach offers high catalytic reactivity and broad functional group compatibility, enabling late-stage fluoroalkylation of drug molecules.

View Article and Find Full Text PDF

Although numerous transition-metal catalyzed cross-coupling reactions of alkenyl electrophiles with a sulfur(VI) leaving group, mainly alkenyl sulfones, have been developed, most rely heavily on highly nucleophilic Grignard reagents, and the use of organoboron reagents remains challenging. We report herein facile preparation and the following Pd-catalyzed Suzuki-Miyaura cross-coupling reaction of alkenyl sulfoximine, a monoaza analog of sulfone. The condensation of alkyl sulfoximine with aldehydes, developed in this study, makes alkenyl sulfoximines more readily available.

View Article and Find Full Text PDF

Amino alcohols are vital in natural products, pharmaceuticals and agrochemicals, and as key building blocks for various applications. Traditional synthesis methods often rely on polar bond retrosynthetic analysis, requiring extensive protecting group manipulations that complicate direct access. Here we show a streamlined approach using a serine-derived chiral carboxylic acid in stereoselective electrocatalytic decarboxylative transformations, enabling efficient access to enantiopure amino alcohols.

View Article and Find Full Text PDF

All-carbon quaternary and tertiary stereocenters connected at the C2-position of functionalizable C3-alkylated indole nucleus are commonly occurring frameworks found in many indole alkaloids of medicinal importance. Their direct access is scarcely reported, a long-standing problem, and developing a unique yet simple method can pave the pathway to an entirely different retrosynthetic route for the total synthesis of these alkaloids. Herein, this problem is addressed by developing an unprecedented branch-selective allylation strategy employing a broad range of structurally and electronically different 3-alkenyl-indoles and allylboronic acids.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!