Dual Roles of TBHP-Enabled Regioselective Hydroetherification of (Trifluoromethyl)alkenes with Boronic Acids: Access to α-Trifluoromethyl β-Aryloxy Tertiary Alcohols

Abstract

The three-starting materials four-component reaction of (trifluoromethyl)alkenes, TBHP, and boronic acids is reported, delivering various useful α-trifluoromethyl-β-aryloxy tertiary alcohols in high yields and in an exclusively regioselective hydroetherification manner. TBHP serves as both the oxidant and nucleophile in this reaction, as well as the O-source of the products.

Key words

dual roles - fluorine - alcohol - 1,2-difunctionalization - boronic acid - (trifluoromethyl)alkene - multi-component reactions

• References


For reviews:
• 1a Russo A, Lattanzi A. Synthesis 2009; 1551
• 1b Hu M, Wu W, Jiang H. ChemSusChem 2019; 12: 2911

For selected examples:
• 1c Tang Y, Fan Y, Zhang Y, Li X, Xu X. Synlett 2016; 27: 1860
• 1d Chen Y, Ma Y, Li L, Jiang H, Li Z. Org. Lett. 2019; 21: 1480
• 1e Chen Y, Li L, Ma Y, Li Z. J. Org. Chem. 2019; 84: 5328
• 1f Zhang J, Xiao D, Tan H, Liu W. J. Org. Chem. 2020; 85: 3929
• 1g Mir BA, Rajamanicham S, Begum P, Patel BK. Eur. J. Org. Chem. 2020; 252
• 2a Xia X, Zhu S, Gu Z, Wang H, Li W, Liu X, Liang Y. J. Org. Chem. 2015; 80: 5572
• 2b Cheng J.-K, Loh T.-P. J. Am. Chem. Soc. 2015; 137: 42

For selected examples:
• 3a Nie J, Guo H, Cahard D, Ma J.-A. Chem. Rev. 2011; 111: 455
• 3b Zhang G.-W, Meng W, Ma H, Nie J, Zhang W.-Q, Ma J.-A. Angew. Chem. Int. Ed. 2011; 50: 3538
• 3c Cook AM, Wolf C. Angew. Chem. Int. Ed. 2016; 55: 2929
• 3d Noda H, Amemiya F, Weidner K, Kumagai N, Shibasaki M. Chem. Sci. 2017; 8: 3260
• 3e Zheng Y, Tan Y, Harms K, Marsch M, Riedel R, Zhang L, Meggers E. J. Am. Chem. Soc. 2017; 139: 4322
• 3f Mszar NW, Mikus MS, Torker S, Haeffner F, Hoveyda AH. Angew. Chem. Int. Ed. 2017; 56: 8736
• 3g Zhu C, Zhu R, Zeng H, Chen F, Liu C, Wu W, Jiang H. Angew. Chem. Int. Ed. 2017; 56: 13324
• 3h Zhang H, Buchwald SL. J. Am. Chem. Soc. 2017; 139: 11590
• 3i Gan X, Zhang Q, Jia X, Yin L. Org. Lett. 2018; 20: 1070
• 3j Zhu C, Zeng H, Liu C, Chen F, Jiang H. Org. Lett. 2019; 21: 4900
• 3k Liu C, Zhu C, Cai Y, Jiang H. Angew. Chem. Int. Ed. 2021; 60: in press
• 4 Tian F, Yan G, Yu J. Chem. Commun. 2019; 55: 13486

For selected examples:
• 5a Ichitsuka T, Fujita T, Ichikawa J. ACS Catal. 2015; 5: 5947
• 5b Huang Y, Hayashi T. J. Am. Chem. Soc. 2016; 138: 12340
• 5c Liu Y, Zhou Y, Zhao Y, Qu J. Org. Lett. 2017; 19: 946
• 5d Dai W, Lin Y, Wan Y, Cao S. Org. Chem. Front. 2018; 5: 55
• 5e Wang M, Pu X, Zhao Y, Wang P, Li Z, Zhu C, Shi Z. J. Am. Chem. Soc. 2018; 140: 9061
• 5f Gao P, Yuan C, Zhao Y, Shi Z. Chem 2018; 4: 2201
• 5g Sakaguchi H, Ohashi M, Ogoshi S. Angew. Chem. Int. Ed. 2018; 57: 328
• 5h Lan Y, Yang F, Wang C. ACS Catal. 2018; 8: 9245
• 5i Jang YJ, Rose D, Mirabi B, Lautens M. Angew. Chem. Int. Ed. 2018; 57: 16147
• 5j Lu X, Wang X, Gong T, Pi J, He S, Fu Y. Chem. Sci. 2019; 10: 809
• 5k Lin Z, Lan Y, Wang C. ACS Catal. 2019; 9: 775
• 5l Ding D, Lan Y, Lin Z, Wang C. Org. Lett. 2019; 21: 2723
• 5m Lin Z, Lan Y, Wang C. Org. Lett. 2019; 21: 8316
• 5n Chen F, Xu X, He Y, Huang G, Zhu S. Angew. Chem. Int. Ed. 2020; 59: 5398
• 5o Zhao X, Li C, Wang B, Cao S. Tetrahedron Lett. 2019; 60: 129
• 5p Liu Q, Zhao X, Li J, Cao S. Acta Chim. Sin. 2018; 76: 945

For selected examples:
• 6a Xiao T, Li L, Zhou L. J. Org. Chem. 2016; 81: 7908
• 6b Lang SB, Wiles RJ, Kelly CB, Molander GA. Angew. Chem. Int. Ed. 2017; 56: 15073
• 6c Wu L.-H, Cheng J.-K, Shen L, Shen Z.-L, Loh T.-P. Adv. Synth. Catal. 2018; 360: 3894
• 6d He Y, Anand D, Sun Z, Zhou L. Org. Lett. 2019; 21: 3769
• 6e Phelan JP, Lang SB, Sim J, Berritt S, Peat AJ, Billings K, Fan L, Molander GA. J. Am. Chem. Soc. 2019; 141: 3723
• 6f Anand D, Sun Z, Zhou L. Org. Lett. 2020; 22: 2371
• 7 Zeng H, Zhu C, Liu C, Cai Y, Chen F, Jiang H. Chem. Commun. 2020; 56: 6241
• 8 Weiss M, Sulz-er-Mosse S. PCT Int. Appl WO 2018/091430 A1, 2018

For selected examples:
• 9a Molander GA, Cavalcanti LN. J. Org. Chem. 2011; 76: 623
• 9b Zhu C, Wang R, Flack JR. Org. Lett. 2012; 14: 3494
• 9c Gogoi A, Bora U. Synlett 2012; 23: 1079
• 9d Gogoi P, Bezboruah P, Gogoi J, Boruah RC. Eur. J. Org. Chem. 2013; 7291
• 9e Chen D.-S, Huang J.-M. Synlett 2013; 24: 499
• 9f Guo S, Lu L, Cai H. Synlett 2013; 24: 1712
• 9g Chatterjee N, Goswami A. Tetrahedron Lett. 2015; 56: 1524
• 9h Molloy JJ, Clohessy TA, Irving C, Anderson NA, Lloyd-Jones GC, Watson AJ. B. Chem. Sci. 2017; 8: 1551
• 9i Weng W.-Z, Liang H, Zhang B. Org. Lett. 2018; 20: 4979
• 9j Yin W, Pan X, Leng W, Chen J, He H. Green Chem. 2019; 21: 4614
• 10a Zeng H, Zhu C, Jiang H. Org. Lett. 2019; 21: 1130
• 10b Cai Y, Zeng H, Zhu C, Liu C, Liu G, Jiang H. Org. Front. Chem. 2020; 7: 1260
• 10c Zhu C, Zeng H, Liu C, Cai Y, Fang X, Jiang H. Org. Lett. 2020; 22: 809
• 10d Zeng H, Cai Y, Jiang H, Zhu C. Org. Lett. 2021; 23: 66
• 10e Zeng H, Fang X, Yang Z, Zhu C, Jiang H. J. Org. Chem. 2021; 86: 2810
• 11 Zatolochnaya OV, Gevorgyan V. Org. Lett. 2013; 15: 2562