K2S2O8 promoted dehydrative cross-coupling between α,α-disubstituted allylic alcohols and thiophenols/thiols?
Organic Chemistry Frontiers Pub Date: 2021-04-08 DOI: 10.1039/D1QO00148E
Abstract
Allyl sulfides are important organosulfur compounds. K2S2O8 promoted dehydrative cross-coupling between α,α-disubstituted allylic alcohols and thiophenols/thiols is demonstrated for the first time, which resulted in a wide range of allyl sulfides in good to high yields. Note that this metal-free synthetic method features broad substrate scopes; in addition to thiophenols and thiols, pyrazole, sodium benzenesulfinate, and sodium trifluoromethanesulfinate were also tolerated. Mechanistic studies revealed that a radical addition process might be involved in the reaction.
Recommended Literature
- [1] Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination? Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. SharadaChem. Commun., 2022,58, 1406-1409 10.1039/D1CC06097J
- [2] Fe3O4/PEG-SO3H as a heterogeneous and magnetically-recyclable nanocatalyst for the oxidation of sulfides to sulfones or sulfoxides Saeideh Mirfakhraei,Malak Hekmati,Fereshteh Hosseini Eshbala,Hojat VeisiNew J. Chem., 2018,42, 1757-1761 10.1039/C7NJ02513K
- [3] Excitation energies from ground-state density-functionals by means of generator coordinates A. B. F. da Silva,K. CapellePhys. Chem. Chem. Phys., 2009,11, 4564-4569 10.1039/B902529D
- [4] Emulsion technologies for multicellular tumour spheroid radiation assays? Kay S. McMillan,Anthony G. McCluskey,Annette Sorensen,Marie Boyd,Michele ZagnoniAnalyst, 2016,141, 100-110 10.1039/C5AN01382H
- [5] Dissociation of large gaseous serine clusters produces abundant protonated serine octamer Jacob S. Jordan,Evan R. WilliamsAnalyst, 2021,146, 2617-2625 10.1039/D1AN00273B
- [6] Fe3O4 nanoparticle chains with N-doped carbon coating: magnetotactic bacteria assisted synthesis and high-rate lithium storage? Dan Yang,Yanping Zhou,Xianhong Rui,Jixin Zhu,Ziyang Lu,Eileen Fong,Qingyu YanRSC Adv., 2013,3, 14960-14962 10.1039/C3RA42116C
- [7] Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores? Shun-Ze Zhan,Mian Li,Xiao-Ping Zhou,Dan Li,Seik Weng NgRSC Adv., 2011,1, 1457-1459 10.1039/C1RA00566A
- [8] Exciton manipulation in rippled transition metal dichalcogenides? Chen Long,Ying Dai,Jianwei Li,Hao JinNanoscale, 2020,12, 21124-21130 10.1039/D0NR05602B
- [9] Enabling stable MnO2 matrix for aqueous zinc-ion battery cathodes? Yiding Jiao,Liqun Kang,Jasper Berry-Gair,Kit McColl,Jianwei Li,Haobo Dong,Hao Jiang,Ryan Wang,Furio Corà,Dan J. L. Brett,Ivan P. ParkinJ. Mater. Chem. A, 2020,8, 22075-22082 10.1039/D0TA08638J
- [10] Distinction of trans–cis photoisomers with comparable optical properties in multiple-state photochromic systems – examining a molecule with three azobenzenes via in situ irradiation NMR spectroscopy? Jonas Kind,Lukas Kaltschnee,Martin Leyendecker,Christina M. ThieleChem. Commun., 2016,52, 12506-12509 10.1039/C6CC06771A
Journal Name:Organic Chemistry Frontiers
research_products
-
CAS no.: 89640-58-4