Skip to main content
SpringerLink
Log in

Di(1H-benzo[d][1,2,3]triazol-1-yl)methane: An efficient ligand for copper and amine-free palladium-catalysed Sonogashira coupling reaction

  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

An efficient Pd-catalysed Sonogashira coupling reaction was achieved in the absence of copper and amine with inorganic base using phosphene-free, air stable di(1H-benzo[d][1,2,3]triazol-1-yl)methane as ligand. The cross coupling of electron-rich, electron-defficient and hindered aryl halides with terminal alkynes afforded the internal alkynes in good to excellent yields.

An efficient Pd-catalysed Sonogashira coupling reaction was achieved in the absence of copper and amine with inorganic base using phosphene-free, air stable di(1H-benzo[d][1,2,3]triazol-1-yl)methane as ligand. The cross coupling of electron-rich, electron-neutral, electron-defficient and hindered aryl halides with terminal alkynes afforded internal arylated alkynes in good to excellent yields.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. Reviews on transition metal catalysed reactions, see: (a) Magano J and Dunetz J R 2011 Chem. Rev. 111 2177 and references cited therein; (b) Chen X, Engle K M, Wang D and Yu J Q 2009 Angew. Chem. Int. Ed. 48 5094; (c) Ackermann L, Vicente R and Kapdi A R 2009 Angew. Chem. Int. Ed. 48 9792; (d) Nakamura I and Yamamoto Y 2004 Chem. Rev. 104 2127; (e) Gladysz J A 2011 Chem. Rev. 111 1167

  2. (a) Martin R and Buchwald S L 2008 Acc. Chem. Res. 41 1461; (b) Fu G C 2008 Acc. Chem. Res. 41 1555; (c) Chinchilla R and Njera C 2007 Chem. Rev. 107 874; (d) Molnar A 2011 Chem. Rev. 111 2251; (e) Islam S M, Mondal P, Tuhinab K and Roya A S 2010 J. Chem. Technol. Biotechnol. 85 999 and references cited therein

  3. (a) Suzuki A 2011 Angew. Chem. Int. Ed. 50 6722; (b) Negishi E I 2011 Angew. Chem. Int. Ed. 50 6738; (c) Wu X F, Anbarasan P, Neumann H and Beller M 2010 Angew. Chem. Int. Ed. 49 9047; (d) Niphakis M J and Georg G I 2011 Org. Lett. 13 196; (e) Ioannidou H A, Kizas C and Koutentis P A 2011 Org. Lett. 13 3466; (f) Proutiere F and Schoenebeck F 2011 Angew. Chem. Int. Ed. 50 8192

  4. (a) Paterson I, Davies R D M and Marquez R 2001 Angew. Chem. Int. Ed. 40 603; (b) Yoshimura F, Kawata S and Hirama M 1999 Tetrahedron Lett. 40 8281; (c) Graham A E, McKerrecher D, Davies D H and Taylor R J K 1996 Tetrahedron Lett. 37 7445; (d) Nicolaou K C and Dai W M 1991 Angew. Chem. Int. Ed. Engl. 30 1387; (e) Maier M E 1995 Synlett. Issue 1 13; (f) Grissom J W, Gunawardena G U, Kingberg D and Huang D 1996 Tetrahedron 52 6453; (g) Bunz U H F 2000 Chem. Rev. 100 1605; (h) Tour J M 2000 Acc. Chem. Res. 33 791; (i) Brunsveld L, Meijer E W, Prince R B and Moore J S 2001 J. Am. Chem. Soc. 123 7978

  5. For reviews, see the following: (a) Sonogashira, K. In Metal-catalyzed cross-coupling reactions 1998; F Diederich and P J Stang (eds); New York: Wiley-VCH; Chapter 5; pp 203; (b) Doucet H and Hierso J C 2007 Angew.Chem. Int. Ed. 46 834; (c) Chinchilla R and Najera C 2007 Chem. Rev. 107 874; (d) Negishi E I and Anastasia L 2003 Chem. Rev. 103 1979

  6. (a) Sonogashira K, Tohda Y and Hagihara N 1975 Tetrahedron Lett. 16 4467; (b) Cassar L 1975 J. Organomet. Chem. 93 253; (c) Dieck H A and Heck F R 1975 J. Organomet. Chem. 93 259

  7. For selected papers on the palladium/phosphine/CuI/ amine system for the Sonogashira cross-coupling reactions, see: (a) Thorand S and Krause N 1998 J. Org. Chem. 63 8551; (b) Hundertmark T, Litter A F, Buchwald S L and Fu G C 2000 Org. Lett. 2 1729; (c) Hierso J C, Fihri A, Amardeil R and Meunier P 2004 Org. Lett. 6 3473; (d) Novák Z, Szabó A, Répási J and Kotschy A 2003 J. Org. Chem. 68 3327; (e) Son S U, Jang Y, Park J, Na H B, Park H M, Yun H J, Lee J and Hyeon T 2004 J. Am. Chem. Soc. 126 5026; (f) Adjabeng G, Brenstrum T, Frampton C S, Robertson A J, Hillhous J, McNulty J and Capretta A 2004 J. Org. Chem. 69 5082; (g) Elangovan A, Wang Y H and Ho T I 2003 Org. Lett. 5 1841; (h) Remmele H, Köllhofer A and Plenio H 2003 Organometallics 22 4098; (i) Batey R A, Shen M and Lough A 2002 Org. Lett. 4 1411; (j) Lee D H, Jung J Y and Jin M J 2010 Green. Chem. 12 2024; (k) Roy S and Plenio H 2010 Adv. Synth. Catal. 352 1014

  8. For selected papers on Pd/Ligand and copper free conditions (a) Choudary B M, Madhi S, Chowsari N S, Kantam M L and Sreedhar B 2002 J. Am. Chem. Soc. 124 14127; (b) Herrmann W A 2002 Angew. Chem., Int. Ed. 41 1290; (d) Nájera C, Gil-Moltó J, Karlström S and Falvello L R 2003 Org. Lett. 5 1451; (e) Soheili A, Albaneze-Walker J, Murry J A, Dormer P G and Hughes D L 2003 Org. Lett. 5 4191; (f) Rau S, Lamm K, Goerls H, Schoeffel J and Walther D 2004 J. Organomet. Chem. 689 3582; (h) Alonso D A, Botella L, Najera C and Pacheco M C 2004 Synthesis 10 1713; (j) Wolf C and Lerebours R 2004 Org. Biomol. Chem. 22 161; (l) Fukuyama T, Shinmen M, Nishitani S, Sato M and Ryu I 2002 Org. Lett. 4 1691; (m) Böhm V P and Hermann W A 2000 Eur. J. Org. Chem. Issue 22 3679; (n) Méry D, Heuzé K and Astruc D 2003 Chem. Commun. Issue 15 1934; (o) Nájera C, Gil-Moltó J, Karlström S and Falvello L R 2003 Org. Lett. 5 1451; (p) Alonso D A, Nájera C and Pacheco M C 2003 Adv. Synth. Catal. 345 1146; (q) Ngassa F N, Gomez J M, Haines B E, Ostach M J, Hector J W, Hoogenboom L J and Page C E 2010 Tetrahedron 66 7919; (r) Chen H J, Lin Z Y, Li M Y, Lian R J, Xue Q W, Chung J L, Chen S C and Chen Y J 2010 Tetrahedron 66 7755; (s) Fleckenstein C A and Plenio H 2008 Green. Chem. 10 563; (t) Islam S M, Mondal P, Roy A S, Mondal S and Hossain D 2010 Tetrahedron Lett. 51 2067; (u) Kuang Y Y and Chen F E 2009 Helv. Chim. Acta 92 897

  9. Pignolet L H (ed) 1983 Homogeneous catalysis with metal phosphine complexes, New York; Plenum

    Google Scholar 

  10. (a) Siemsen P, Livingston R C and Diederich F 2000 Angew. Chem. Int. Ed. 39 2632; (b) Li J H, Liang Y and Zhang X D 2005 Tetrahedron 61 1903

  11. (a) Li J H, Zhang X D and Xie Y X 2005 Eur. J. Org. Chem. Issue 20 4256; (b) Liang Y, Xie Y X and Li J H 2006 J. Org. Chem. 71 379; (c) Yi C and Hua R 2006 J. Org. Chem. 71 2535

  12. (a) Liang B, Dai M, Chen J and Yang Z 2005 J. Org. Chem. 70 391; (b) Mino T, Shirae Y, Saito T, Sakamoto M and Fujita T 2006 J. Org. Chem. 71 9499; (c) Komaromi A and Novak Z 2008 Chem. Commun. Issue 40 4968 and references therein

  13. (a) Verma A K, Singh J, Sankar V K, Chaudhary R and Chandra R 2007 Tetrahedron Lett. 48 4207; (b) Verma A K, Singh J and Chaudhary R 2007 Tetrahedron Lett. 48 7199; (c) Verma A K, Kesharwani T, Singh J, Tandon V and Larock R C 2009 Angew. Chem., Int. Ed. 39 2632; (d) Verma A K, Singh J and Larock R C 2009 Tetrahedron 65 8434; (e) Jha R R, Chaudhary R, Chandra R and Verma A K 2011 J. Indian Chem. Soc. 88 1; (f) Verma A K, Rustagi V, Aggarwal T and Singh A P 2010 J. Org. Chem. 75 7691; (g) Verma A K, Joshi M and Singh V P 2011 Org. Lett. 13 1630; (h) Verma A K, Shukla S P, Singh J and Rustagi V 2011 J. Org. Chem. 76 5670

Download references

Author information

Authors and Affiliations

  1. Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi, Delhi, 110007, India

    JASPAL SINGH & AKHILESH KUMAR VERMA

Authors
  1. JASPAL SINGH
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. AKHILESH KUMAR VERMA
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to AKHILESH KUMAR VERMA.

Electronic Supplementary Material

Below is the link to the electronic supplementary material.

(DOC 7.56 MB)

Rights and permissions

Reprints and permissions

About this article

Cite this article

SINGH, J., VERMA, A.K. Di(1H-benzo[d][1,2,3]triazol-1-yl)methane: An efficient ligand for copper and amine-free palladium-catalysed Sonogashira coupling reaction. J Chem Sci 123, 937–942 (2011). https://doi.org/10.1007/s12039-011-0174-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-011-0174-4

Keywords

Search

Navigation