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-00000084.xml
Synthesis 2019; 51(10): 2171-2182
DOI: 10.1055/s-0037-1612216
DOI: 10.1055/s-0037-1612216
paper
Copper-Catalyzed N-Arylation of Sulfoximines with Arylboronic Acids under Mild Conditions
J.K. gratefully acknowledges DST-India (DST/INT/MPG/P-09/2016) and Max-Planck Society, Germany for financial support through Indo-Max Planck partner group project. S.G. and S.B. acknowledge IIT (BHU) for a research fellowship.Further Information
Publication History
Received: 07 December 2018
Accepted after revision: 16 January 2019
Publication Date:
19 February 2019 (online)
![](https://www.thieme-connect.de/media/synthesis/201910/lookinside/thumbnails/ss-2018-t0825-op_10-1055_s-0037-1612216-1.jpg)
Abstract
N-Arylation of sulfoximines with different arylboronic acids, including sterically hindered boronic acids, is achieved using copper(I) iodide and 4-DMAP at room temperature. Moreover, N-arylation of biologically relevant l-methionine sulfoximine is demonstrated for the first time. All these reactions provided the desired products in excellent yields within a short span of time. The optimized reaction conditions are well suited to the task of N-vinylation of sulfoximine with trans-2-phenylvinylboronic acid.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1612216.
- Supporting Information
- CIF File
-
References
- 1a Reggelin M, Zur C. Synthesis 2000; 1
- 1b Lucking U. Angew. Chem. Int. Ed. 2013; 52: 9399
- 1c Frings M, Bolm C, Blum A, Gnamm C. Eur. J. Med. Chem. 2017; 126: 225
- 1d Bizet V, Kowalczyk R, Bolm C. Chem. Soc. Rev. 2014; 43: 2426
- 2a Bolm C. Sulfoximines as Ligands in Asymmetric Metal Catalysis. In Asymmetric Synthesis with Chemical and Biological Methods. Enders D, Jaeger K.-E. Wiley-VCH; Weinheim: 2007
- 2b Remy P, Langner M, Bolm C. Org. Lett. 2006; 8: 1209
- 2c Langner M, Bolm C. Angew. Chem. Int. Ed. 2004; 43: 5984
- 2d Sedelmeier J, Hammerer T, Bolm C. Org. Lett. 2008; 10: 917
- 2e Frings M, Thome I, Bolm C. Beilstein J. Org. Chem. 2012; 8: 1443
- 3 Vessally E, Mohammadi R, Hosseinian A, Didehban K, Edjlali L. J. Sulfur Chem. 2018; 39: 674
- 4a Sedelmeier J, Bolm C. J. Org. Chem. 2005; 70: 6904
- 4b Bolm C, Hildebrand JP. J. Org. Chem. 2000; 65: 169
- 4c Cho GY, Remy P, Jansson J, Moessner C, Bolm C. Org. Lett. 2004; 6: 3293
- 4d Correa A, Bolm C. Adv. Synth. Catal. 2008; 350: 391
- 4e Yongpruksa N, Calkins NL, Harmata M. Chem. Commun. 2011; 47: 7665
- 4f Harmata M, Hong X, Ghosh SK. Tetrahedron Lett. 2004; 45: 5233
- 5 Moessner C, Bolm C. Org. Lett. 2005; 7: 2667
- 6a Bolm C, Hildebrand JP, Rudolph J. Synthesis 2000; 911
- 6b Yang Q, Choy PY, Zhao Q, Leung MP, Chan HS, So CM, Wong WT, Kwong FY. J. Org. Chem. 2018; 83: 11369
- 7 Kim J, Ok J, Kim S, Choi W, Lee PH. Org. Lett. 2014; 16: 4602
- 8 Aithagani SK, Dara S, Munagala G, Aruri H, Yadav M, Sharma S, Vishwakarma RA, Singh PP. Org. Lett. 2015; 17: 5547
- 9 Vaddula B, Leazer J, Varma RS. Adv. Synth. Catal. 2012; 354: 986
- 10a Wang L, Priebbenow DL, Dong W, Bolm C. Org. Lett. 2014; 16: 2661
- 10b Lämmermann H, Sudau A, Rackl D, Weinmann H, Collins K, Wortmann L, Candish L, Hog D, Meier R. Synlett 2018; 29: 2679
- 11a Chan DM. T, Monaco KL, Wang RP, Winters MP. Tetrahedron Lett. 1998; 39: 2933
- 11b Lam PY. S, Clark CG, Saubern S, Adams J, Winters MP, Chan DM. T, Combs A. Tetrahedron Lett. 1998; 39: 2941
- 12 Hendriks CM. M, Bohmann RA, Bohlem M, Bolm C. Adv. Synth. Catal. 2014; 356: 1847
- 13 Gupta S, Chaudhary P, Muniyappan N, Sabiah S, Kandasamy J. Org. Biomol. Chem. 2017; 15: 8493
- 14a Bedford RB, Hazelwood SL, Limmert ME, Brown JM, Ramdeehul S, Cowley AR, Coles SJ, Hursthouse MB. Organometallics 2003; 22: 1364
- 14b Surry DS, Buchwald SL. Chem. Sci. 2010; 1: 13
- 14c Bhunia S, Pawar GG, Kumar SV, Jiang YW, Ma DW. Angew. Chem. Int. Ed. 2017; 56: 16136
- 14d Hamann BC, Hartwig JF. J. Am. Chem. Soc. 1998; 120: 7369
- 14e Roy S, Sarma MJ, Kashyap B, Phukan P. Chem. Commun. 2016; 52: 1170
- 14f Vantourout JC, Law RP, Isidro-Llobet A, Atkinson SJ, Watson AJ. B. J. Org. Chem. 2016; 81: 3942
- 15a Raghuvanshi K, Zell D, Ackermann L. Org. Lett. 2017; 19: 1278
- 15b Kumar KA, Kannaboina P, Rao DN, Das P. Org. Biomol. Chem. 2016; 14: 8989
- 16a Brusilow WS. A, Peters TJ. Expert Opin. Ther. Targets 2017; 21: 461
- 16b Buglioni L, Bizet V, Bolm C. Adv. Synth. Catal. 2014; 356: 2209
- 16c Griffith OW. J. Biol. Chem. 1982; 257: 13704
- 17a Dehli JR, Bolm C. Adv. Synth. Catal. 2005; 347: 239
- 17b Hetzer RH, Gais HJ, Raabe G. Synthesis 2008; 1126
- 17c Ikeda M, Tsubouchi H, Tsunekawa M, Kondo H, Tamura Y. Chem. Pharm. Bull. 1984; 32: 3028
- 18a Zenzola M, Doran R, Degennaro L, Luisi R, Bull JA. Angew. Chem. Int. Ed. 2016; 55: 7203
- 18b Lohier J.-F, Glachet T, Marzag H, Gaumont A.-C, Reboul V. Chem. Commun. 2017; 53: 2064
- 18c Tota A, Zenzola M, Chawner SJ, St John-Campbell S, Carlucci C, Romanazzi G, Degennaro L, Bull JA, Luisi R. Chem. Commun. 2017; 53: 348