Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2020; 31(20): 2039-2042
DOI: 10.1055/s-0040-1706298
DOI: 10.1055/s-0040-1706298
letter
Practical Transition-Metal-Free Protodeboronation of Arylboronic Acids in Aqueous Sodium Hypochlorite
This work was financially supported by the Yunnan Provincial Science and Technology Department-Applied Basic Research Joint Special Funds of Yunnan University of Chinese Medicine [2017FF117(-023)].
Abstract
A concise and practical method was developed for the protodeboronation of arylboronic acids under mild conditions in aqueous NaClO at 100 °C. The strategy is low-cost, transition-metal-free, and base-free.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706298.
- Supporting Information
Publication History
Received: 03 August 2020
Accepted after revision: 26 August 2020
Article published online:
07 October 2020
© 2020. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References and Notes
- 1a Biffis A, Centomo P, Del Zotto A, Zecca M. Chem. Rev. 2018; 118: 2249
- 1b West MJ, Fyfe JW. B, Vantourout JC, Watson AJ. B. Chem. Rev. 2019; 119: 12491
- 1c Wu L, Shen J, Yang G, Zhang W. Tetrahedron Lett. 2018; 59: 4055
- 1d Moustafa D, Sweet C, Lim H, Calalpa B, Kaur P. Tetrahedron Lett. 2018; 59: 3816
- 1e Chen D, Liu J.-G, Zhang X, Xu M.-H. Synlett 2019; 30: 1693
- 1f Zhang Z, Yu Y, Xie Y, Hughes T, Xu J, Huang F, Huang H. Green Chem. 2020; 22: 4165
- 1g Wang H.-R, Huang E.-H, Luo C, Luo W.-F, Xu Y, Qian P.-C, Zhou J.-M, Ye L.-W. Chem. Commun. 2020; 56: 4832
- 2a Zhao H, Mao G, Han H, Song J, Liu Y, Chu W, Sun Z. RSC Adv. 2016; 6: 41108
- 2b Haesuwannakij S, Yakiyama Y, Sakurai H. ACS Catal. 2017; 7: 2998
- 2c Cao Y.-N, Tian X.-C, Chen X.-X, Gao F, Zhou X.-L. Synlett 2017; 28: 601
- 2d Lee DS, Cho EJ. Org. Biomol. Chem. 2019; 17: 4317
- 2e Ostrowska S, Rogalski S, Lorkowski J, Walkowiak J, Pietraszuk C. Synlett 2018; 29: 1735
- 2f Valiente A, Carrasco S, Sanz-Marco A, Tai C.-W, Gómez AB, Martín-Matute B. ChemCatChem 2019; 11: 3933
- 3a Hesse MJ, Butts CP, Willis CL, Aggarwal VK. Angew. Chem. Int. Ed. 2012; 51: 12444
- 3b Nave S, Sonawane RP, Elford TG, Aggarwal VK. J. Am. Chem. Soc. 2010; 132: 17096
- 4a Watson CG, Aggarwal VK. Org. Lett. 2013; 15: 1346
- 4b Roesner S, Casatejada JM, Elford TG, Sonawane RP, Aggarwal VK. Org. Lett. 2011; 13: 5740
- 5a Xu W, Li M, Qiao L, Xie J. Chem. Commun. 2020; 56: 8524
- 5b Trowbridge A, Walton SM, Gaunt MJ. Chem. Rev. 2020; 120: 2613
- 5c Xia Y, Qiu D, Wang J. Chem. Rev. 2017; 117: 13810
- 6 Ainley AD, Challenger F. J. Chem. Soc. 1930; 2171
- 7 Klingensmith LM, Bio MM, Moniz GA. Tetrahedron Lett. 2007; 48: 8242
- 8 Lai R.-Y, Chen C.-L, Liu S.-T. J. Chin. Chem. Soc. (Weinheim, Ger.) 2006; 53: 979
- 9 Liu C, Li X, Wu Y, Qiu J. RSC Adv. 2014; 4: 54307
- 10 Liu C, Li X, Wu Y. RSC Adv. 2015; 5: 15354
- 11a Noonan G, Leach AG. Org. Biomol. Chem. 2015; 13: 2555
- 11b Cox PA, Reid M, Leach AG, Campbell AD, King EJ, Lloyd-Jones GC. J. Am. Chem. Soc. 2017; 139: 13156
- 12 Li M.-X, Tang Y.-L, Gao H, Mao Z.-W. Tetrahedron Lett. 2020; 61: 151784
- 13a Lee C.-Y, Ahn S.-J, Cheon C.-H. J. Org. Chem. 2013; 78: 12154
- 13b Zhang G, Li Y, Liu J. RSC Adv. 2017; 7: 34959
- 14 Protodeboronation of Arylboronic Acids; General Procedure A solution of the appropriate arylboronic acid (1 mmol) and TBAB (64 mg, 0.2 mmol) in 10.5 wt% aq NaClO was stirred at 100 °C for 6–12 h until the reaction was complete (TLC). The mixture was extracted with Et2O (2 × 5 mL), and the organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography [silica gel, PE–EtOAc (40:1 to 20:1)]. 1,4-Dimethoxybenzene (2a) Prepared from 1a according to the general procedure as a white solid; yield: 121 mg (88%); mp 51–53 °C. 1H NMR (400 MHz, CDCl3): δ = 6.86 (s, 4 H), 3.78 (s, 6 H).