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 2016; 27(06): 951-955
DOI: 10.1055/s-0035-1561291
DOI: 10.1055/s-0035-1561291
letter
Copper-Catalyzed Amidation of Arylboronic Acids with Nitriles
Further Information
Publication History
Received: 03 October 2015
Accepted after revision: 22 November 2015
Publication Date:
11 December 2015 (online)
Abstract
A copper-catalyzed amidation of arylboronic acids with nitriles has been developed. This reaction provides an efficient and complementary methodology for the synthesis of various N-arylamides with a broad substrate scope.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561291.
- Supporting Information
-
References and Notes
- 1a Zhang D.-W, Zhao X, Hou J.-L, Li Z.-T. Chem. Rev. 2012; 112: 5271
- 1b Allen CL, Williams JM. J. Chem. Soc. Rev. 2011; 40: 3405
- 1c Valeur E, Bradley M. Chem. Soc. Rev. 2009; 38: 606
- 1d Tew GN, Liu D, Chen B, Doerksen RJ, Kaplan J, Carroll PJ, Klein ML, DeGrado WF. Proc. Natl. Acad. Sci. U.S.A. 2002; 99: 5110
- 2a Thomas AM, Sujatha A, Anilkumar G. Mini-Rev. Org. Chem. 2015; 12: 3
- 2b Jiang Y, Ma D In Catalysis without Precious Metals. Bullock RM. Wiley-Blackwell; Weinheim: 2010: 213-233
- 2c Wang Y, Zeng J, Cui X. Chin. J. Org. Chem. 2010; 30: 181 ; in Chinese
- 3a Downs EL, Tyler DR. Coord. Chem. Rev. 2014; 280: 28
-
3b Ahmed TJ, Knapp SM. M, Tyler DR. Coord. Chem. Rev. 2011; 255: 949
- 4a Chemat F, Poux M, Berlan J. J. Chem. Soc., Perkin Trans. 2 1996; 1781
- 4b Siegfried L, Comparone A, Neuburger M, Kaden TA. Dalton Trans. 2005; 30
- 4c Sahnoun S, Messaoudi S, Peyrat J.-F, Brion J.-D, Alami M. Tetrahedron Lett. 2012; 53: 2860
- 4d Li Z, Wang L, Zhou X. Adv. Synth. Catal. 2012; 354: 584
- 4e Hirano T, Uehara K, Kamata K, Mizuno N. J. Am. Chem. Soc. 2012; 134: 6425
- 4f Tomás-Mendivil E, García-Álvarez R, Vidal C, Crochet P, Cadierno V. ACS Catal. 2014; 4: 1901
- 4g Tomás-Mendivil E, Suárez FJ, Díez J, Cadierno V. Chem. Commun. 2014; 50: 9661
- 4h Tomás-Mendivil E, Menéndez-Rodríguez L, Francos J, Crochet P, Cadierno V. RSC Adv. 2014; 4: 63466
- 4i Tong P, Yang D, Li Y, Wang B, Qu J. Organometallics 2015; 34: 3571
- 4j Midya GC, Kapat A, Maiti S, Dash J. J. Org. Chem. 2015; 80: 4148
- 4k Matsuoka A, Isogawa T, Morioka Y, Knappett BR, Wheatley AE. H, Saito S, Naka H. RSC Adv. 2015; 5: 12152
- 5a Xiang S.-K, Zhang D.-X, Hu H, Shi J.-L, Liao L.-G, Feng C, Wang B.-Q, Zhao K.-Q, Hu P, Yang H, Yu W.-H. Adv. Synth. Catal. 2013; 355: 1495
- 5b Zhang D.-X, Xiang S.-K, Hu H, Tan W, Feng C, Wang B.-Q, Zhao K.-Q, Hu P, Yang H. Tetrahedron 2013; 69: 10022
- 5c Wang J, Yin X, Wu J, Wu D, Pan Y. Tetrahedron 2013; 69: 10463
- 6a Karad SN, Liu R.-S. Angew. Chem. Int. Ed. 2014; 53: 5444
- 6b Xiang S.-K, Tan W, Zhang D.-X, Tian X.-L, Feng C, Wang B.-Q, Zhao K.-Q, Hu P, Yang H. Org. Biomol. Chem. 2013; 11: 7271
- 6c Rao B, Zeng X. Org. Lett. 2014; 16: 314
- 6d Hosseini-Sarvari M, Khanivar A, Moeini F. J. Mater. Sci. 2015; 50: 3065
- 6e Yu J, Xia Y, Lu M. Appl. Organomet. Chem. 2014; 28: 764
-
6f Okamoto S, Sugiyama Y. Synlett 2013; 24: 1044
- 6g Prasad Tulichala RN, Kumara Swamy KC. Chem. Commun. 2015; 51: 12008
- 6h Mani NS, Fitzgerald AE. J. Org. Chem. 2014; 79: 8889
- 6i Zhao J, Zhang S, Zhang W, Xi Z. Organometallics 2014; 33: 8
- 6j Kang B, Fu Z, Hong SH. J. Am. Chem. Soc. 2013; 135: 11704
- 6k Hu C, Yan X, Zhou X, Li Z. Org. Biomol. Chem. 2013; 11: 8179
- 7 Xiang S.-K, Li J.-M, Huang H, Feng C, Ni H.-L, Chen X.-Z, Wang B.-Q, Zhao K.-Q, Hu P, Redshaw C. Adv. Synth. Catal. 2015; 357: 3435
- 8 Surya Prakash GK, Moran MD, Mathew T, Olah GA. J. Fluorine Chem. 2009; 130: 806
- 9 General Procedure Cu(OTf)2 (10.8 mg, 0.03 mmol) and phenylboronic acid (1a, 36.6 mg, 0.3 mmol) were placed into a 25 mL Schlenk tube equipped with a magnetic stir bar. To this mixture were added in sequence DCE (1.0 mL, contains 0.1% v/v H2O), benzonitrile (2a, 36.8 μL, 0.36 mmol), BF3·OEt2 (75 μL, 0.6 mmol), and MesI(OAc)2 (163.8 mg, 0.45 mmol, dissolved in 1.0 mL of DCE containing 0.1% v/v H2O) with an injection syringe under stirring under an argon atmosphere. After the reaction mixture was stirred for 2 h at 90 °C, TMSOTf (108 μL, 0.6 mmol) was added with an injection syringe. After stirring again for 2 h, H2O (16 μL, 0.9 mmol) was added, and the reaction was carried out for additional 20 h. The solution was cooled to r.t. and quenched by the addition of H2O (20 mL) and extracted with CH2Cl2 (3 × 10 mL). The organic layer was dried over anhydrous MgSO4 and concentrated in vacuum. The residue was purified by column chromatography on silica gel (eluent: PE–EtOAc–CH2Cl2, 7:1:1) to afford the product 3aa. IR (KBr): νmax = 3345, 1656, 1579, 1259, 751, 690 cm–1. 1H NMR (400 MHz, CDCl3): δ = 7.89–7.86 (m, 2 H), 7.84 (s, 1 H), 7.65 (d, J = 7.6 Hz, 2 H), 7.58–7.53 (m, 1 H), 7.52–7.47 (m, 2 H), 7.41–7.36 (m, 2 H), 7.16 (t, J = 7.2 Hz, 1 H) ppm. 13C NMR (100 MHz, DMSO-d 6): δ = 165.5, 139.1, 134.9, 131.5, 128.5, 128.3, 127.6, 123.6, 120.3. ESI-MS: m/z = 198.1 [M + H]+.
- 10a Bielawski M, Aili D, Olofsson B. J. Org. Chem. 2008; 73: 4602
- 10b Zhu M, Jalalian N, Olofsson B. Synlett 2008; 592
- 11a Ichiishi N, Canty AJ, Yates BF, Sanford MS. Org. Lett. 2013; 15: 5134
- 11b Ichiishi N, Canty AJ, Yates BF, Sanford MS. Organometallics 2014; 33: 5525
- 11c Lv T, Wang Z, You J, Lan J, Gao G. J. Org. Chem. 2013; 78: 5723
- 11d Skucas E, MacMillan DW. C. J. Am. Chem. Soc. 2012; 134: 9090
-
11e Phipps RJ, Grimster NP, Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 8172
For reviews, see:
For reviews, see:
For some selected examples, see: