Synthesis of 2‐Aryl‐2‐hydroxyethyl Dithiocarbamates via Regioselective Addition of Tetraalkylthiuram Disulfides to Styrenes under Transition‐Metal‐Free Conditions

Abstract

This paper describes a method for the synthesis of 2-aryl-2-hydroxyethyl dithiocarbamates via difunctionalization of alkenes involving CÀ S and CÀ O bonds formation with tetraalkylthiuram disulfides as the functional reagents. The reaction proceeded well under transition-metal-free conditions and afforded up to 88% yield of the desired products. Numerous useful functional groups were tolerated under the reaction conditions. This methodology provides a direct approach to β-hydroxy dithiocarbamates, featuring readily available starting materials and broad substrate scope, which shows its practical synthetic value in organic synthesis.

Copper-Promoted Hiyama Cross-Coupling of Arylsilanes With Thiuram Reagents: A Facile Synthesis of Aryl Dithiocarbamates

“…Considering the experimental evidence as well the previous reports ( Lu et al, 2020 ; Dong et al, 2017 ; Luo et al, 2020 ; Hao et al, 2020 ; Lai et al, 2019b ), a plausible reaction mechanism was tentatively proposed and described in Scheme 4 . Firstly, the coordination of 1, 10-phenanthroline with copper salts to produce the copper complex A.…”

Nickel-Catalyzed Amidation of Aryl Alkynyl Acids with Tetraalkylthiuram Disulfides: A Facile Synthesis of Aryl Alkynyl Amides

“…At the outset of our investigation, phenylpropiolic acid (1a) and tetramethylthiuram disulfide (TMTD,2a) were chosen as the model substrates to optimize the reaction conditions, and the results were summarized in Table 1. First, the effect of catalysts has been studied.…”

Copper-Catalyzed Three-Component Synthesis of β-Hydroxysulfides from Styrene Oxide, Aryl Iodide, and Carbon Disulfide

“…1-Phenyl-2-(thiophen-2-ylthio)ethan-1-ol (3ax). 21 Yellow viscous liquid (19.8 mg, 42% yield); petroleum ether/ethyl acetate = 5/1 as an eluent. 1 H NMR (400 MHz, chloroform-d) δ 7.40−7.38 (m, 1H), 7.35−7.32 (m, 4H), 7.31−7.28 (m, 1H), 7.20−7.17 (m, 1H), 7.02− 6.99 (m, 1H), 4.74 (d, J = 9.4 Hz, 1H), 3.16 (dd, J = 13.8, 3.4 Hz, 1H), 2.97 (dd, J = 13.7, 9.6 Hz, 1H), 2.84 (s, 1H).…”