The bifunctional reaction of styrene derivatives with alcohols, ketones, nitriles, ethers, thioethers and other solvent molecules is a radical relay reaction discovered and developed by Wang Naixing's research group since 2012. A persistent and stable radical (free radical on the carbon atom adjacent to the benzene ring) is generated during the reaction duo to the p-π conjugation effect of the benzene ring, this reaction is called thes Wang reaction since 2018. This effective reaction can realize the high value conversion of the styrene derivatives through one-step reaction, which is of great significance for the new synthesis methods of drugs and intermediates.
[1] Lan X W, Wang N X, Xing Y.Recent advances in radical difunctionalization of simple alkenes[J].European Journal of Organic Chemistry, 2017, 2017(39):5821-5851.
[2] Zhang T, Wu Y H, Wang N X, et al.Advances in C(sp3)-H Bond functionalization via radical processes[J].Synthesis 2019, 51(24):4531-4548.
[3] Wang N X, Zhang L Y, Wu Y H, et al.C(sp3)-H bond functionalization of alcohols, ketones, nitriles, ethers and amides using tert-butyl hydroperoxide as a radical initiator[J].Synlett, 2021, 32(1):23-29.
[4] Zhang J X, Wang Y J, Zhang W, et al.Selective nickeland manganese-catalyzed decarboxylative cross coupling of α, β-unsaturated carboxylic acids with cyclic ethers[J].Science Reports, 2014, 4(1):7446-7451.
[5] Zhang T, Lan X W, Zhou Y Q, et al.C(sp3)-H bond functionalization of non-cyclic ethers by decarboxylative oxidative coupling with α, β-unsaturated carboxylic acids[J].Science China Chemistry, 2018, 61(2):180-183.
[6] Zhang J X, Wang Y J, Wang N X, et al.Nickel-Catalyzed sp3 C-H bond activation from decarboxylative cross-coupling of α, β-unsaturated carboxylic acids with amides[J].Synlett, 2014, 25(11):1621-1625.
[7] Zhang W, Wang N X, Bai C B, et al.Manganese-mediated coupling reaction of vinylarenes and aliphatic alcohols[J].Scientific Reports, 2015, 5(1):15250-15257.
[8] Lan X W, Wang N X, Zhang W, et al.Copper/Manganese Co-catalyzed oxidative coupling of vinylarenes with ketones[J].Organic Letters, 2015, 17(18):4460-4463.
[9] Lan X W, Wang N X, Bai C B, et al.Unactivated C(sp3)-H bond functionalization of alkyl nitriles with vinylarenes and mechanistic studies[J].Organic Letters, 2016, 18(23):5986-5989.
[10] Yan Z, Wang N X, Gao X W, et al.A copper (II) acetate mediated oxidative-coupling of styrenes and ethers through an unactivated C(sp3)-H bond functionalization.Advanced Synthesis & Catalysis, 2019, 361(5):1007-1011.
[11] Yan Z, Wang N X, Zhang L Y, et al.Studies on the C (sp3)-H bond functionalization of thioethers with styrenes[J].Organic & Biomolecular Chemistry,.2022, 20, 5845-5851.
[12] Fischer H.The persistent radical effect:A principle for selective radical reactions and living radical polymerizations[J].Chemical Reviews, 2001, 101(12):3581-3610.
[13] Leifert D, Studer A.The persistent radical effect in organic synthesis[J].Angewandte Chemie-International Edition, 2020, 59:74-108.
[14] Lu S L, Qi L Y, Li Z P.Cobalt-Catalyzed alkylationperoxidation of alkenes with 1, 3-dicarbonyl compounds and T-hydro[J].Asian Journal of Organic Chemistry, 2017, 6(3):313-321.
[15] Xue Q C, Xie J, Xu P, et al.Metal-Free, n-Bu4NI-catalyzed regioselective difunctionalization of unactivated alkenes[J].ACS Catalysis, 2013, 3(6):1365-1368.
[16] Kornblum N, DeLaMare H E.The base catalyzed decomposition of a dialkyl peroxide[J].Journal of the American Chemical Society, 1951, 73:880-881.
[17] Takai K, Oshima K, Nozaki H.Selective oxidation with t-butyl hydroperoxide and aluminium reagents[J].Tetrahedron Letters, 1980, 21(17):1657-1660.
[18] Zhou Y Q, Wang N X, Zhou S B, et al.[4+3] cycloaddition of aromatic α, β-unsaturated aldehydes and ketones with epoxides:One-Step approach to synthesize seven-membered oxacycles catalyzed by lewis acid[J].Journal of Organic Chemistry, 2011, 76(2):669-672.
[19] Zhou S B, Zhou Y Q, Xing Y L, et al.Exploration on asymmetric synthesis of flavanone catalyzed by (S)-pyrrolidinyl tetrazole[J].Chirality, 2011, 23(7):504-506.
[20] Hong X W, Zhou Y Q, Bai C B, et al.Asymmetric synthesis of 1, 3-oxazolidine derivatives with multi-component reaction and research of kinetic resolution[J].Molecules, 2015, 20(9):17208-17220.
[21] Huang Z, Zhang J C, Zhou Y Q, et al.Enantioselective friedel-crafts alkylation reaction of thiophenes with ethyl glyoxylate:An easy access to chiral secondary alcohols[J].European Journal of Organic Chemistry, 2011, 5:843-847.
