A Palladium-Catalyzed Three-Component Synthesis of Arylmethylsulfonamides

Tamara Beisel; Georg Manolikakes

doi:10.1055/s-0035-1560910

Synthesis, Table of Contents

Synthesis 2016; 48(03): 379-386
DOI: 10.1055/s-0035-1560910

paper

A Palladium-Catalyzed Three-Component Synthesis of Arylmethylsulfonamides

Tamara Beisel

Department of Organic Chemistry and Chemical Biology, Goethe-University Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany Email: g.manolikakes@chemie.uni-frankfurt.de

,

Georg Manolikakes*

Department of Organic Chemistry and Chemical Biology, Goethe-University Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany Email: g.manolikakes@chemie.uni-frankfurt.de

› Author Affiliations

Abstract

All articles of this category

Abstract

A palladium-catalyzed three-component synthesis of arylmethylsulfonamide derivatives from sulfonamides, paraformaldehyde, and arylboronic acids has been developed. The method is operationally simple and provides rapid access to a broad range of structurally interesting sulfonamidomethyl compounds.

Key words

multicomponent reactions - palladium - sulfonamides - Petasis–Borono–Mannich reactions - paraformaldehyde - arylboronic acids

Full Text

References

References

1a Ballatore C, Soper JH, Piscitelli F, James M, Huang L, Atasoylu O, Huryn DM, Trojanowski JQ, Lee VM.-Y, Brunden KR, Smith AB. J. Med. Chem. 2011; 54: 6969
1b Cole DC, Lennox WJ, Lombardi S, Ellingboe JW, Bernotas RC, Tawa GJ, Mazandarani H, Smith DL, Zhang G, Coupet J, Schechter LE. J. Med. Chem. 2005; 48: 353
1c Drews J. Science 2000; 287: 1960
1d Koehler NK. U, Yang C.-Y, Varady J, Lu Y, Wu X.-W, Liu M, Yin D, Bartels M, Xu B.-y, Roller PP, Long Y.-q, Li P, Kattah M, Cohn ML, Moran K, Tilley E, Richert JR, Wang S. J. Med. Chem. 2004; 47: 4989
1e Natarajan A, Guo Y, Harbinski F, Fan Y.-H, Chen H, Luus L, Diercks J, Aktas H, Chorev M, Halperin JA. J. Med. Chem. 2004; 47: 4979
1f Nirogi RV. S, Daulatabad AV, Parandhama G, Mohammad S, Sastri KR, Shinde AK, Dubey PK. Bioorg. Med. Chem. Lett. 2010; 20: 4440

2a Derry CJ, Derry S, Moore RA. Cochrane Database Syst. Rev. 2014; 5: CD009108 ; DOI: 10.1002/14651858.CD009108.pub2
2b Holmes CP, Li X, Pan Y, Xu C, Bhandari A, Moody CM, Miguel JA, Ferla SW, de Francisco MN, Frederick BT, Zhou S, Macher N, Jang L, Irvine JD, Grove JR. Bioorg. Med. Chem. Lett. 2005; 15: 4336
2c Malwal SR, Sriram D, Yogeeswari P, Konkimalla VB, Chakrapani H. J. Med. Chem. 2012; 55: 553
2d Northrup AB, Katcher MH, Altman MD, Chenard M, Daniels MH, Deshmukh SV, Falcone D, Guerin DJ, Hatch H, Li C, Lu W, Lutterbach B, Allison TJ, Patel SB, Reilly JF, Reutershan M, Rickert KW, Rosenstein C, Soisson SM, Szewczak AA, Walker D, Wilson K, Young JR, Pan B.-S, Dinsmore CJ. J. Med. Chem. 2013; 56: 2294

3a de Boer TJ, Backer HJ. Org. Synth., Coll. Vol. IV . Wiley; London: 1963: 943
3b Harmata M, Zheng P, Huang C, Gomes MG, Ying W, Rayanil K.-O, Ranyanil K.-O, Balan G, Calkins NL. J. Org. Chem. 2007; 72: 683
3c Kamal A, Reddy JS, Bharathi EV, Dastagiri D. Tetrahedron Lett. 2008; 49: 348
3d Rattanaburi P, Khumraksa B, Pattarawarapan M. Tetrahedron Lett. 2012; 53: 2689
3e Sridhar R, Srinivas B, Kumar VP, Narender M, Rao KR. Adv. Synth. Catal. 2007; 349: 1873

4a Caddick S, Wilden JD, Judd DB. J. Am. Chem. Soc. 2004; 126: 1024
4b de Luca L, Giacomelli G. J. Org. Chem. 2008; 73: 3967

5a Pan X, Gao J, Liu J, Lai J, Jiang H, Yuan G. Green Chem. 2015; 17: 1400
5b Wei W, Liu C, Yang D, Wen J, You J, Wang H. Adv. Synth. Catal. 2015; 357: 987
5c Zhao J, Xu J, Chen J, Wang X, He M. RSC Adv. 2014; 4: 64698

6 García Ruano JL, Parra A, Yuste F, Mastranzo VM. Synthesis 2008; 311

7a Abdel-Magid AF, Carson KG, Harris BD, Maryanoff CA, Shah RD. J. Org. Chem. 1996; 61: 3849
7b Blackwell JM, Sonmor ER, Scoccitti T, Piers WE. Org. Lett. 2000; 2: 3921
7c Chase PA, Welch GC, Jurca T, Stephan DW. Angew. Chem. Int. Ed. 2007; 46: 8050

8a Hamid M, Haniti SA, Allen CL, Lamb GW, Maxwell AC, Maytum HC, Watson AJ. A, Williams JM. J. J. Am. Chem. Soc. 2009; 131: 1766
8b Pan J, Li J.-q, Huang R.-f, Zhang X.-h, Shen H, Xiong Y, Zhu X.-m. Synthesis 2015; 47: 1101
8c Qu P, Sun C, Ma J, Li F. Adv. Synth. Catal. 2014; 356: 447
8d Shi F, Tse MK, Zhou S, Pohl M.-M, Radnik J, Hübner S, Jähnisch K, Brückner A, Beller M. J. Am. Chem. Soc. 2009; 131: 1775
8e Zhu M, Fujita K.-i, Yamaguchi R. Org. Lett. 2010; 12: 1336

9 Molander GA, Fleury-Brégeot N, Hiebel M.-A. Org. Lett. 2011; 13: 1694

10a Candeias NR, Montalbano F, Cal PM. S. D, Gois PM. P. Chem. Rev. 2010; 110: 6169
10b Petasis NA, Akritopoulou I. Tetrahedron Lett. 1993; 34: 583

11 Beisel T, Manolikakes G. Org. Lett. 2015; 17: 3162

12a Aizina YA, Rozentsveig IB, Levkovskaya GG, Mirskova AN. Russ. J. Org. Chem. 2003; 39: 1334
12b Hayashi T, Kawai M, Tokunaga N. Angew. Chem. Int. Ed. 2004; 43: 6125
12c Katritzky AR, Hanci S, Meher NK. ARKIVOC 2009; (iv): 115

13a Leermann T, Leroux FR, Colobert F. Org. Lett. 2011; 13: 4479
13b Tang S, Liu M, Gu C, Zhao Y, Lu P, Lu D, Liu L, Shen F, Yang B, Ma Y. J. Org. Chem. 2008; 73: 4212

14 Bhattacharyya S, Gooding OW, Labadie J. Tetrahedron Lett. 2003; 44: 6099
15 Chakravarti R, Mano A, Iwai H, Aldeyab SS, Kumar RP, Kantam ML, Vinu A. Chem. Eur. J. 2011; 17: 6673
16 Baslé E, Jean M, Gouault N, Renault J, Uriac P. Tetrahedron Lett. 2007; 48: 8138
17 Burlingham BT, Widlanski TS. J. Am. Chem. Soc. 2001; 123: 2937
18 Laha JK, Dayal N, Jain R, Patel K. J. Org. Chem. 2014; 79: 10899

Supplementary Material

Supporting Information