2020
DOI: 10.1002/adsc.202000729
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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 re… Show more

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Cited by 15 publications
(5 citation statements)
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“…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.…”
Section: Resultssupporting
confidence: 54%
“…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.…”
Section: Resultssupporting
confidence: 54%
“…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.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…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).…”
Section: -((35-dimethylphenyl)thio)-1-phenylethan-1-ol (3av) 11amentioning
confidence: 99%