Catalyst-free hydrothiolation of alkynes with dithiocarbamic acids?
Chemical Communications Pub Date: 2019-01-02 DOI: 10.1039/C8CC09726G
Abstract
A highly regio- and stereocontrolled procedure for the synthesis of vinyl dithiocarbamates via catalyst-free hydrothiolation of unactivated alkynes with in situ prepared dithiocarbamic acids with total atom economy is reported. While unactivated terminal alkynes afforded the Markovnikov adducts with excellent regioselectivity, ethynyltrimethylsilane furnished the E-selective anti-Markovnikov adducts with excellent regio- and stereoselectivity. In addition, the obtained vinyl dithiocarbamates were applied as efficient precursors for the synthesis of secondary thiols and α-hydroxythioamides.
Recommended Literature
- [1] An asymmetric supercapacitor based on controllable WO3 nanorod bundle and alfalfa-derived porous carbon? Kanjun Sun,Fengting Hua,Shuzhen Cui,Yanrong Zhu,Hui Peng,Guofu MaRSC Adv., 2021,11, 37631-37642 10.1039/D1RA04788D
- [2] An alkynylboronatecycloaddition strategy to functionalised benzyne derivatives? James D. Kirkham,Patrick M. Delaney,George J. Ellames,Eleanor C. Row,Joseph P. A. HarrityChem. Commun., 2010,46, 5154-5156 10.1039/C0CC01345E
- [3] An atlas of endohedral Sc2S cluster fullerenes? Li-Hua Gan,Rui Wu,Jian-Lei Tian,Patrick W. FowlerPhys. Chem. Chem. Phys., 2017,19, 419-425 10.1039/C6CP07370K
- [4] An approach to biodegradable star polymeric architectures using disulfide coupling? Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. DavisChem. Commun., 2008, 6582-6584 10.1039/B817037A
- [5] An artificial CO-releasing metalloprotein built by histidine-selective metallation? Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?oChem. Commun., 2015,51, 3993-3996 10.1039/C4CC10204E
- [6] An amplified fluorescence detection of T4 polynucleotide kinase activity based on coupled exonuclease III reaction and a graphene oxide platform? Ni-Na Sun,Fengli Qu,Xiaobing Zhang,Shufang Zhang,Jinmao YouAnalyst, 2015,140, 1827-1831 10.1039/C4AN01953A
- [7] An integrated microfluidic 3D tumor system for parallel and high-throughput chemotherapy evaluation? Dan Liu,Rui Hu,Zhongchao Huang,Meilin Sun,Kai HanAnalyst, 2020,145, 6447-6455 10.1039/D0AN01229G
- [8] An analyte-triggered artificial peroxidase system based on dimanganese complex for a versatile enzyme assay? Suji Lee,Min Su HanChem. Commun., 2021,57, 9450-9453 10.1039/D1CC03638F
- [9] An amorphous Cu–In–S nanoparticle-based precursor ink with improved atom economy for CuInSe2 solar cells with 10.85% efficiency? Green Chem., 2017,19, 1268-1277 10.1039/C6GC03280J
- [10] Aggregation, pretransitional behavior, and optical properties in the isotropic phase of lyotropic chromonic liquid crystals studied in high magnetic fields Tanya Ostapenko,Peter J. Collings,Samuel N. Sprunt,J. T. GleesonSoft Matter, 2013,9, 9487-9498 10.1039/C3SM51819A
Journal Name：Chemical Communications
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)