Skip to main content

Advertisement

SpringerLink
Log in

1,2,3-Triazole N(2)-coordinated C–O coupling: Access to ortho aryloxyl 1,4-diaryl 1,2,3-triazoles

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

Abstract

CuI-catalyzed selective Ullmann C–O coupling of 1,4-disubstituted 1,2,3-triazole bromides with phenols were achieved through the coordination of N(2) atom. The ortho C–Br bond in N(1) aryl can be selectively coupled with phenols, while other C–Br bonds remain inert, generating ortho aryloxyl 1,4-diaryl 1,2,3-triazoles.

CuI-catalyzed selective Ullmann C–O couplings of 1,4-disubstituted 1,2,3-triazole bromides with phenols were achieved through the coordination of N(2) atom in triazole. The ortho C-Br bond in N(1) of aryl can be selectively coupled with phenols, while other C-Br bonds remain inert, generating ortho-aryloxyl 1,4-diaryl 1,2,3-triazoles.

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

Figure 1
Scheme 1
Scheme 2

References

  1. (a) Asakawa Y and Matsuda R 1982 Riccardin C, a novel cyclic bibenzyl derivative from Reboulia hemisphaerica Phytochemistry 21 2143; (b) Kosenkova Y S, Polovinka M P, Komarova N I, Korchagina D V, Kurochnika N Y, Cheremushnika V A and Salakhutdinov N F 2007 Riccardin C, a bisbibenzyl compound from Primula macrocalyx Chem. Nat. Compd. 43 712; (c) Morita D, Sawada H, Ogawa W, Miyachi H and Kuroda T 2015 Riccardin C derivatives cause cell leakage in Staphylococcus aureus Biochim. Biophys. Acta 1848 2057

  2. (a) Chemburkar S R, Deming K C and Reddy R E 2010 Chemistry of thyroxine: an historical perspective and recent progress on its synthesis Tetrahedron 66 1955; (b) Lass N and Reinehr T 2015 Low treatment adherence in pubertal children treated with thyroxin or growth hormone Horm. Res. Paediat. 84 240

  3. Gosh S, Kumar A S, Mehta G N, Soundararajan R and Sen S 2009 Formal synthesis of piperazinomycin, a novel antifungal antibiotic ARKIVOC 72

  4. Pagliai F, Pirali T, Del Grosso E, Di Brisco R, Tron G C, Sorba G and Genazzani A A 2006 Rapid synthesis of triazole-modified resveratrol analogues via click chemistry J. Med. Chem. 49 467

    Article  CAS  Google Scholar 

  5. For selected reviews on diaryl ethers synthesis, please see: (a) Frlan R and Kikelj D 2006 Recent progress in diaryl ether synthesis Synthesis 2271; (b) Ley S V and Thomas A W 2003 Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation Angew. Chem. Int. Ed. 42 5400; (c) Monnier F and Taillefer M 2009 Catalytic C-C, C-N, and C–O Ullmann-type coupling reactions Angew. Chem. Int. Ed. 48, 6954; (d) Lefèvre G, Franc G, Tlili A, Adamo C, Taillefer M, Ciofini I and Jutand A 2012 Contribution to the mechanism of copper-catalyzed C-N and C–O bond formation Organometallics 31 7694

  6. (a) Palucki M, Wolfe J P and Buchwald S L 1997 Palladium-catalyzed intermolecular carbon-oxygen bond formation: A new synthesis of aryl ethers J. Am. Chem. Soc. 119 3395; (b) Mann G, Incarvito C, Rheingold A L and Hartwig J F 1999 Palladium-catalyzed C–O coupling involving unactivated aryl halides. Sterically induced reductive elimination to form the C–O bond in diaryl ethers J. Am. Chem. Soc. 121 3224

  7. (a) Marcoux J F, Doye S and Buchwald S L 1997 A general copper-catalyzed synthesis of diaryl ethers J. Am. Chem. Soc. 119 10539; (b) Ma D and Cai Q 2003 N,N-Dimethyl glycine-promoted Ullmann coupling reaction of phenols and aryl halides Org. Lett. 5 3799; (c) Cristau H J, Cellier P P, Hamada S, Spindler J F and Taillefer M 2004 A general and mild Ullmann-type synthesis of diaryl ethers Org. Lett. 6 913

  8. (a) Xu J, Mu X, Chen P, Ye J and Liu G 2014 Copper-catalyzed trifluoromethylthiolation of aryl halides with diverse directing groups Org. Lett. 16 3942; (b) Ziegler D, Choi J, Muñoz-Molina J, Bissember A C, Peters J C and Fu G C 2013 A versatile approach to Ullmann C-N couplings at room temperature: New families of nucleophiles and electrophiles for photoinduced, copper-catalyzed processes J. Am. Chem. Soc. 135 13107; (c) Niu J, Zhou H, Li Z, Xu J and Hu S 2008 An efficient Ullmann-type C–O bond formation catalyzed by an air-stable copper(I)-bipyridyl complex J. Org. Chem. 73 7814; (d) Naidu A B, Jaseer E A and Sekar G 2009 General, mild, and intermolecular Ullmann-type synthesis of diaryl and alkyl aryl ethers catalyzed by diol-copper(I) complex J. Org. Chem. 74 3675

  9. (a) Xu M, Kuang C, Wang Z, Yang Q and Jiang Y 2011 A novel approach to 1-monosubstituted 1,2,3-triazoles by a click cycloaddition/decarboxylation process Synthesis 223; (b) Jiang Y, Kuang C and Yang Q 2011 Facile and quick synthesis of 1-monosubstituted aryl 1,2,3-triazoles: a copper-free [3 + 2] cycloaddition Tetrahedron 67 289; (c) Wu L, Xie Y, Chen Z, Niu Y and Liang Y, 2009 A convenient synthesis of 1-substituted 1,2,3-triazoles via CuI/Et 3N catalyzed ‘click chemistry’ from azides and acetylene gas Synlett 1453

  10. (a) Bai H, Cai Z, Wang S and Ji S 2015 Aerobic oxidative cycloaddition of α-chlorotosylhydrazones with arylamines: General chemoselective construction of 1,4-disubstituted and 1,5-disubstituted 1,2,3-triazoles under metal-free and azide-free conditions Org. Lett. 17 2898; (b) Deraedt C, Pinaud N and Astruc D 2014 Recyclable catalytic dendrimer nanoreactor for part-per-million CuI catalysis of “click” chemistry in water J. Am. Chem. Soc. 136 12092; (c) Wang Y, Xie Y, Qu H, Wang H, Pan Y and Huang F 2014 Ce(OTf) 3-catalyzed [3 + 2] cycloaddition of azides with nitroolefins: Regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles J. Org. Chem. 79 4463; (d) Cheng G, Zeng X, Shen J, Wang X and Cui 2013 A metal-free multicomponent cascade reaction for the regiospecific synthesis of 1,5-disubstituted 1,2,3-triazoles Angew. Chem. Int. Edit. 52 13265; (e) Rostovtsev V V, Green L G, Fokin V V and Sharpless K B 2002 A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes Angew. Chem. Int. Edit. 33 45

  11. (a) Wang X, Zhang L, Krishnamurthy D, Senanayake C H and Wipf P 2010 General solution to the synthesis of N-2-substituted 1,2,3-triazoles Org. Lett. 12 4632; (b) Guru M M and Punniyamurthy T 2012 Copper(II)-catalyzed aerobic oxidative synthesis of substituted 1,2,3- and 1,2,4-triazoles from bisarylhydrazones via C-H functionalization/C-C/N-N/C-N bonds formation J. Org. Chem. 77 5063; (c) Yan W, Liao T, Tuguldur O, Zhong C, Petersen J L and Shi X 2011 Mitsunobu reaction of 1,2,3-NH-triazoles: A regio- and stereoselective approach to functionalized triazole derivatives Chem. Asian J. 6 2720; (d) Yamajala K D B, Patil M and Banerjee S 2015 Pd-catalyzed regioselective arylation on the C-5 position of N-Aryl 1,2,3-triazoles J. Org. Chem. 80 3003

  12. (a) Sirivolu V R, Vernekar S K V, Ilina T, Myshakina N S, Parniak M A and Wang Z 2013 Clicking 3 ′-azidothymidine into novel potent inhibitors of human immunodeficiency virus J. Med. Chem. 56 8765; (b) Ferreira da Costa J, Garcia-Mera X, Caamano O, Brea J M and Loza M I 2015 Synthesis by microwave-assisted 1,3-dipolar cycloaddition of 1,2,3-triazole 1’-homo-3’-isoazanucleosides and evaluation of their anticancer activity Eur. J. Med. Chem. 98 212; (c) Zhang H, Wei J, Vijaya Kumar K, Rasheed S and Zhou C 2015 Synthesis and biological evaluation of novel D-glucose-derived 1,2,3-triazoles as potential antibacterial and antifungal agents Med. Chem. Res. 24 182; (d) He C and Shreeve J M 2015 Energetic materials with promising properties: Synthesis and characterization of 4,4-bis(5-nitro-1,2,3-2H-triazole) derivatives Angew. Chem. In. Edit. 54 6260; (e) Padalkar V S, Lanke S K, Chemate S B and Sekar N J 2015 N-2-aryl-1,2,3-triazoles: A novel class of blue emitting fluorophores-synthesis, photophysical properties study and DFT computations Fluoresc. 25 985; (f) Obadia M M, Colliat-Dangus G, Debuigne A, Serghei A, Detrembleur C and Drockenmuller E 2015 Poly(vinyl ester 1,2,3-triazolium)s: A new member of the poly(ionic liquid)s family Chem. Commun. 51 3332; (g) Krikorian M, Liu S and Swager T M 2014 Columnar liquid crystallinity and mechanochromism in cationic platinum(II) complexes J. Am. Chem. Soc. 136 2952

  13. (a) Tian Q, Chen X, Liu W, Wang Z, Shi S and Kuang C 2013 Regioselective halogenation of 2-substituted-1,2,3-triazoles via sp2 C-H activation Org. Biomol. Chem. 11 7830; (b) Shi S, Liu W, He P and Kuang C 2014 Regioselective halogenation of 2-substituted-1,2,3-triazoles via sp2 C-H activation Org. Biomol. Chem. 12 3576; (c) Shi S and Kuang C 2014 Palladium-catalyzed ortho-alkoxylation of 2-aryl-1,2,3-triazoles J. Org. Chem. 79 6105; (d) Wang Z, Tian Q, Yu X and Kuang C 2014 Palladium-catalyzed acylation of 2-aryl-1,2,3-triazoles with aldehydes Adv. Synth. Catal. 356 961; (e) Wang Z and Kuang C 2014 Palladium-catalyzed acyloxylation of 2-substituted 1,2,3-triazoles via direct sp2 C-H bond activation Adv. Synth. Catal. 356 1549; (f) Liu W, Li Y, Xu B and Kuang C 2013 Palladium-catalyzed olefination and arylation of 2-substituted 1,2,3-triazole N-oxides Org. Lett. 15 2342; (g) Yu X, Huang Z, Liu W, Shi S and Kuang C 2015 Palladium-catalyzed oxidative C-H/C-H cross-coupling of 1-substituted 1,2,3-triazoles with furans and thiophenes Org. Biomol. Chem. 13 4459; (h) He P, Tian Q and Kuang C 2015 Palladium-catalyzed ortho-C-H alkenylation of 2-benzyl-1,2,3-triazoles Org. Biomol. Chem. 13 7146

  14. (a) Zhao S, Yu R, Chen W, Liu M and Wu H 2015 Efficient approach to mesoionic triazolo[5,1-a]isoquinolium through rhodium-catalyzed annulation of triazoles and internal alkynes Org. Lett. 17 2828; (b) Li X, Liu K, Zou G and Liu P 2014 Ruthenium-catalyzed alkenylation of arenes with alkynes or alkenes by 1,2,3-triazole-directed C-H activation Eur. J. Org. Chem. 2014 7878; (c) Irastorza A, Aizpurua J and Correa A 2016 Triazole-directed Pd-catalyzed C(sp2)-H oxygenation of arenes and alkenes Org. Lett. 18 1080

  15. (a) Ribas X and Güell I 2014 Cu(I)/Cu(III) catalytic cycle involved in Ullmann-type cross-coupling reactions Pure Appl. Chem. 86 345; (b) Sung S, Sale D, Braddock D C, Armstrong A, Brennan C and Davies R P 2016 Mechanistic studies on the copper-catalyzed N-arylation of alkylamines promoted by organic soluble ionic bases ACS Catal. 6 3965

Download references

Acknowledgements

We are grateful for the financial support provided by the National Natural Science Foundation of China (Grant Nos. 21262020 and 21662020).

Author information

Authors and Affiliations

  1. Faculty of Science, Kunming University of Science and Technology, Kunming, 650500, China

    YAOWEN LIU, FEN ZHAO, HAOHUA ZHOU, KAI XIE & YUBO JIANG

Authors
  1. YAOWEN LIU
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. FEN ZHAO
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. HAOHUA ZHOU
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. KAI XIE
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. YUBO JIANG
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to YUBO JIANG.

Additional information

Supplementary Information (SI)

Experimental procedures, characterization data and all the NMR spectra are available at www.ias.ac.in/chemsci.

Electronic supplementary material

Below is the link to the electronic supplementary material.

(DOCX 2.54 MB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

LIU, Y., ZHAO, F., ZHOU, H. et al. 1,2,3-Triazole N(2)-coordinated C–O coupling: Access to ortho aryloxyl 1,4-diaryl 1,2,3-triazoles. J Chem Sci 129, 289–294 (2017). https://doi.org/10.1007/s12039-017-1240-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-017-1240-3

Keywords

Search

Navigation