Cobalt(II) catalytic oxidation of arylmethyl sulfonyl imines to arylcarbonyl analogues
Zetao Ma A , Peipei Ma A , Hongli Wu A and Haifeng Gan A *A
Abstract
A novel Co(OAc)2/N-hydroxyphthalimide (NHPI)-catalyzed oxidation of 3-arylmethyl sulfonyl imines to prepare 3-arylcarbonyl analogues has been realized. 3-Arylcarbonyl sulfonyl imines were comprehensively synthesized from benzyl substrates for the first time. The reactions proceeded in moderate to excellent yields. Mechanistic investigation suggests that 3-(hydroperoxy(phenyl)methyl)benzo[d]isothiazole 1,1-dioxide A is the key intermediate for the formation of products 2.
Keywords: Co(OAc)2, dioxygen, mechanism, NHPI, oxidation, pharmaceutical, radical, sulfonyl imines.
References
1 Jeran M, Cotman AE, Stephan M, Mohar B. Stereopure functionalized benzosultams via ruthenium(II)-catalyzed dynamic kinetic resolution–asymmetric transfer hydrogenation. Org Lett 2017; 19: 2042-2045.
| Crossref | Google Scholar | PubMed |
2 Yu C-B, Wang D-W, Zhou Y-G. Highly enantioselective synthesis of sultams via Pd-catalyzed hydrogenation. J Org Chem 2009; 74: 5633-5635.
| Crossref | Google Scholar | PubMed |
3 Wang H, Jiang T, Xu M-H. Simple branched sulfur–olefins as chiral ligands for Rh-catalyzed asymmetric arylation of cyclic ketimines: highly enantioselective construction of tetrasubstituted carbon stereocenters. J Am Chem Soc 2013; 135: 971-974.
| Crossref | Google Scholar | PubMed |
4 Li Q, Yuan X, Li B, Wang B. The regioselective annulation of alkylidenecyclopropanes by Rh(III)-catalyzed C–H/C–C activation to access spirocyclic benzosultams. Chem Commun 2020; 56: 1835-1838.
| Crossref | Google Scholar |
5 Clerici F, Gelmi ML, Yokoyama K, Pocar D, Van Voorhis WC, Buckner FS, Gelb MH. Isothiazole dioxides: synthesis and inhibition of Trypanosoma brucei protein farnesyltransferase. Bioorg Med Chem Lett 2002; 12: 2217-2220.
| Crossref | Google Scholar | PubMed |
6 Zhang X, Chen J, Gao Y, Li K, Zhou Y, Sun W, Fan B. Photocatalyzed transfer hydrogenation and deuteriation of cyclic N-sulfonylimines. Org Chem Front 2019; 6: 2410-2414.
| Crossref | Google Scholar |
7 Tan C-M, Chen GS, Chen C-S, Chang P-T, Chern J-W. Design, synthesis and biological evaluation of benzo[1.3.2]dithiazolium ylide 1,1-dioxide derivatives as potential dual cyclooxygenase-2/5-lipoxygenase inhibitors. Bioorg Med Chem 2011; 19: 6316-6328.
| Crossref | Google Scholar | PubMed |
8 Elsayed MSA, El-Araby ME, Serya RAT, El-Khatib AH, Linscheid MW, Abouzid KAM. Structure-based design and synthesis of novel pseudosaccharine derivatives as antiproliferative agents and kinase inhibitors. Eur J Med Chem 2013; 61: 122-131.
| Crossref | Google Scholar | PubMed |
9 Liu R-R, Wang D-J, Wu L, Xiang B, Zhang G-Q, Gao J-R, Jia Y-X. Nickel-catalyzed enantioselective addition of styrenes to cyclic N-sulfonyl α-ketiminoesters. ACS Catal 2015; 5: 6524-6528.
| Crossref | Google Scholar |
10 Azevedo CMG, Watterson KR, Wargent ET, Hansen SVF, Hudson BD, Kępczyńska MA, Dunlop J, Shimpukade B, Christiansen E, Milligan G, Stocker CJ, Ulven T. Non-acidic free fatty acid receptor 4 agonists with antidiabetic activity. J Med Chem 2016; 59: 8868-8878.
| Crossref | Google Scholar | PubMed |
11 An Q, Liu D, Shen J, Liu Y, Zhang W. The construction of chiral fused azabicycles using a Pd-catalyzed allylic substitution cascade and asymmetric desymmetrization strategy. Org Lett 2017; 19: 238-241.
| Crossref | Google Scholar | PubMed |
12 Zhang H-M, Jia W-Q, Liang Z-Q, Ye S. N-heterocyclic carbene-catalyzed [3+3] cyclocondensation of bromoenals and ketimines: highly enantioselective synthesis of dihydropyridinones. Asian J Org Chem 2014; 3: 462-465.
| Crossref | Google Scholar |
13 Kravina AG, Mahatthananchai J, Bode JW. Enantioselective, NHC-catalyzed annulations of trisubstituted enals and cyclic N-sulfonylimines via α,β-unsaturated acyl azoliums. Angew Chem Int Ed Engl 2012; 51: 9433-9436.
| Crossref | Google Scholar | PubMed |
14 Jiang T, Wang Z, Xu M-H. Rhodium-catalyzed asymmetric arylation of cyclic N-sulfonyl aryl alkyl ketimines: efficient access to highly enantioenriched α-tertiary amines. Org Lett 2015; 17: 528-531.
| Crossref | Google Scholar | PubMed |
15 Liu Z-P. Synthesis of enantiomerically pure (+)- and (-)-3-methyl-3-(2-naphthyl)-2H-benzo[e][1,2]thiazine 1,1,4-triones. Heterocycles 2007; 71: 1843-1849.
| Crossref | Google Scholar |
16 Hruszkewycz DP, Miles KC, Thiel OR, Stahl SS. Co/NHPI-mediated aerobic oxygenation of benzylic C–H bonds in pharmaceutically relevant molecules. Chem Sci 2017; 8: 1282-1287.
| Crossref | Google Scholar | PubMed |
17 Zhang Y, Riemer D, Schilling W, Kollmann J, Das S. Visible-light-mediated efficient metal-free catalyst for α-oxygenation of tertiary amines to amides. ACS Catal 2018; 8: 6659-6664.
| Crossref | Google Scholar |
18 Gan H, Lu Y, Huang Y, Ni L, Xu J, Yao H, Wu X. Oxidation of 1-benzyldihydroisoquinolines or 1-benzyltetrahydroisoquinolines with dioxygen to 1-benzoylisoquinolines. Tetrahedron Lett 2011; 52: 1320-1324.
| Crossref | Google Scholar |
19 Niu K, Shi X, Ding L, Liu Y, Song H, Wang Q. HCl-catalyzed aerobic oxidation of alkylarenes to carbonyls. ChemSusChem 2022; 15: e202102326.
| Crossref | Google Scholar | PubMed |
20 Wang H, Liu J, Qu J-P, Kang Y-B. Overcoming electron-withdrawing and product-inhibition effects by organocatalytic aerobic oxidation of alkylpyridines and related alkylheteroarenes to ketones. J Org Chem 2020; 85: 3942-3948.
| Crossref | Google Scholar | PubMed |
21 Recupero F, Punta C. Free radical functionalization of organic compounds catalyzed by N-hydroxyphthalimide. Chem Rev 2007; 107: 3800-3842.
| Crossref | Google Scholar | PubMed |
22 Ishii Y, Sakaguchi S, Iwahama T. Innovation of hydrocarbon oxidation with molecular oxygen and related reactions. Adv Synth Catal 2001; 343: 393-427.
| Crossref | Google Scholar |
23 Yoshino Y, Hayashi Y, Iwahama T, Sakaguchi S, Ishii Y, et al. Catalytic oxidation of alkylbenzenes with molecular oxygen under normal pressure and temperature by N-hydroxyphthalimide combined with Co(OAc)2. J Org Chem 1997; 62: 6810-6813.
| Crossref | Google Scholar |
24 Sakaguchi S, Shibamoto A, Ishii Y. Remarkable effect of nitrogen dioxide for N-hydroxyphthalimide-catalyzed aerobic oxidation of methylquinolines. Chem Commun 2002; 2002(2): 180-181.
| Crossref | Google Scholar | PubMed |
25 He Y-G, Huang Y-K, Fan Q-Q, Zheng B, Luo Y-Q, Zhu X-L, Shi X-X. Copper(II)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)–H bonds adjacent to 3,4-dihydroisoquinolines using air (O2) as a clean oxidant. RSC Adv 2021; 11: 29702-29710.
| Crossref | Google Scholar | PubMed |