Pd-Catalyzed Cascade Reaction for the Synthesis of 2-Substituted Indoles

Jagannath Jadhav; Vipul Gaikwad; Rajanikant Kurane; Rajashri Salunkhe; Gajanan Rashinkar

doi:10.1055/s-0032-1317320

Synlett, Table of Contents

Synlett 2012; 23(17): 2511-2515
DOI: 10.1055/s-0032-1317320

letter

Pd-Catalyzed Cascade Reaction for the Synthesis of 2-Substituted Indoles

Jagannath Jadhav

Department of Chemistry, Shivaji University, Kolhapur 416004, M.S., India, Fax: +91(231)2692333 Email: gsr_chem@unishivaji.ac.in

,

Vipul Gaikwad

Department of Chemistry, Shivaji University, Kolhapur 416004, M.S., India, Fax: +91(231)2692333 Email: gsr_chem@unishivaji.ac.in

,

Rajanikant Kurane

Department of Chemistry, Shivaji University, Kolhapur 416004, M.S., India, Fax: +91(231)2692333 Email: gsr_chem@unishivaji.ac.in

,

Rajashri Salunkhe

Department of Chemistry, Shivaji University, Kolhapur 416004, M.S., India, Fax: +91(231)2692333 Email: gsr_chem@unishivaji.ac.in

,

Gajanan Rashinkar*

Department of Chemistry, Shivaji University, Kolhapur 416004, M.S., India, Fax: +91(231)2692333 Email: gsr_chem@unishivaji.ac.in

› Author Affiliations

Abstract

All articles of this category

Abstract

An efficient cascade methodology toward the synthesis of 2-substituted indoles has been developed. The transformation proceeds via a palladium-catalyzed cross-coupling reaction of o-nitrobenzyl cyanides with boronic acids. The use of Fe as co-catalyst during the course of reaction employs significant enhancement in reaction rates. The developed protocol allows for the unprecedented use of arylboronic acids as coupling partners for constructing 2-substituted indoles.

Key words

cascade synthesis - 2-substituted indoles - palladium-catalyzed cross-coupling reaction

Full Text

References

References
1 Humphrey GR, Kuethe JT. Chem. Rev. 2006; 106: 2875
2 Denmark SE, Baird JD, Regens CS. J. Org. Chem. 2008; 73: 1440
3 Cacchi S, Fabrizi G. Chem. Rev. 2005; 105: 2873

4a Fraley ME, Hoffman WF, Arrington KL, Hungate RW, Hartman GD, McFall RC, Coll KE, Rickert K, Thomas KA, McGaughey GB. Curr. Med. Chem. 2004; 11: 709
4b Fang YQ, Karisch R, Lautens M. J. Org. Chem. 2007; 72: 1341
4c Palimkar SS, More VS, Harish Kumar P, Srinivasan KV. Tetrahedron 2007; 63: 12786

For reviews of different approaches, see:

5a Taber DF, Tirunahari PK. Tetrahedron 2011; 67: 7195
5b Patil SA, Patil R, Miller DD. Curr. Med. Chem. 2011; 18: 615
5c Cacchi S, Fabrizi G. Org. Biomol. Chem. 2011; 9: 641
5d Cacchi S, Fabrizi G. Chem. Rev. 2011; 111: PR215

6a Rashinkar GS, Salunkhe RS. J. Mol. Catal. A: Chem. 2010; 316: 146
6b Kamble S, Kumbhar A, Rashinkar G, Barge M, Salunkhe R. Ultrason. Sonochem. 2012; 19: 812

7a Zhou CX, Larock RC. J. Am. Chem. Soc. 2004; 126: 2302
7b Zhou CX, Larock RC. J. Org. Chem. 2006; 71: 3551

8 Siu J, Baxendale IR, Ley SV. Org. Biomol. Chem. 2004; 2: 160 ; and references cited therein
9 Katayama S, Ae N, Nagata R. J. Org. Chem. 2001; 66: 3474 ; and references cited therein

10a Larock RC, Tian Q, Pletnev AA. J. Am. Chem. Soc. 1999; 121: 3238
10b Pletnev AA, Larock RC. Tetrahedron Lett. 2002; 43: 2133
10c Pletnev AA, Tian Q, Larock RC. J. Org. Chem. 2002; 67: 9276
10d Zhao L, Lu X. Angew. Chem. Int. Ed. 2002; 41: 4343
10e Zhao B, Lu X. Tetrahedron Lett. 2006; 47: 6765
10f Zhao B, Lu X. Org. Lett. 2006; 8: 5987
10g Ueura K, Miyamura S, Satoh T, Miyaura M. J. Organomet. Chem. 2000; 595: 31
10h Shimizu H, Murakami YC. Chem. Commun. 2007; 2855
10i Wong Y.-C, Parthasarathy K, Cheng C.-H. Org. Lett. 2010; 12: 1736

11 The complex (DMSO)₂Pd(O₂CCF₃)₂ has been well characterized, see: Bancroft DP, Cotton FA, Verbruggen M. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1989; 45: 1289

12a Kraus GA, Guo H. Org. Lett. 2008; 10: 3061
12b Cacchi S, Fabrizi G, Parisi LM. Org. Lett. 2003; 5: 3843
12c Sakai N, Annaka K, Fujita A, Sato A, Konakahara T. J. Org. Chem. 2008; 73: 4160
12d Yamane Y, Liu X, Hamasaki A, Ishida T, Haruta M, Yokoyama T, Tokunaga M. Org. Lett. 2009; 11: 5162
12e Slätt J, Bergman J. Tetrahedron 2002; 58: 9187
12f Zhao J, Zhang Y, Cheng K. J. Org. Chem. 2008; 73: 7428
12g Tsuchimoto T, Matsubayashi H, Kaneko M, Nagase Y, Miyamura T, Shirakawa E. J. Am. Chem. Soc. 2008; 130: 15823
12h Koradin C, Dohle W, Rodriguez AL, Schmid B, Knochel P. Tetrahedron 2003; 59: 1571