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Literature DB >> 15631470

Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates.

Fahmi Himo¹, Timothy Lovell, Robert Hilgraf, Vsevolod V Rostovtsev, Louis Noodleman, K Barry Sharpless, Valery V Fokin.

Abstract

Huisgen's 1,3-dipolar cycloadditions become nonconcerted when copper(I) acetylides react with azides and nitrile oxides, providing ready access to 1,4-disubstituted 1,2,3-triazoles and 3,4-disubstituted isoxazoles, respectively. The process is highly reliable and exhibits an unusually wide scope with respect to both components. Computational studies revealed a stepwise mechanism involving unprecedented metallacycle intermediates, which appear to be common for a variety of dipoles.

Entities: Chemical

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Year: 2005 PMID： 15631470 DOI： 10.1021/ja0471525

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

156 in total

1. α-Azido ketones. Part 7: synthesis of 1,4-disubstituted triazoles by the "click" reaction of various terminal acetylenes with phenacyl azides or α-azidobenzo(hetera)cyclanones.

Authors: Krisztina Kónya; Szabolcs Fekete; Anita Abrahám; Tamás Patonay
Journal: Mol Divers Date: 2012-02-04 Impact factor: 2.943

2. Simple and efficient synthesis of 5'-aryl-5'-deoxyguanosine analogs by azide-alkyne click reaction and their antileishmanial activities.

Authors: Pierre Daligaux; Sébastien Pomel; Karine Leblanc; Philippe M Loiseau; Christian Cavé
Journal: Mol Divers Date: 2016-01-11 Impact factor: 2.943

3. Decarboxylative Alkynylation.

Authors: Joel M Smith; Tian Qin; Rohan R Merchant; Jacob T Edwards; Lara R Malins; Zhiqing Liu; Guanda Che; Zichao Shen; Scott A Shaw; Martin D Eastgate; Phil S Baran
Journal: Angew Chem Int Ed Engl Date: 2017-08-01 Impact factor: 15.336

4. Synthesis of a 10,000-membered library of molecules resembling carpanone and discovery of vesicular traffic inhibitors.

Authors: Brian C Goess; Rami N Hannoush; Lawrence K Chan; Tomas Kirchhausen; Matthew D Shair
Journal: J Am Chem Soc Date: 2006-04-26 Impact factor: 15.419

Review 5. Computational studies on the regioselectivity of metal-catalyzed synthesis of 1,2,3 triazoles via click reaction: a review.

Authors: Tayebeh Hosseinnejad; Bahareh Fattahi; Majid M Heravi
Journal: J Mol Model Date: 2015-09-18 Impact factor: 1.810

6. Observation of the controlled assembly of preclick components in the in situ click chemistry generation of a chitinase inhibitor.

Authors: Tomoyasu Hirose; Nobuo Maita; Hiroaki Gouda; Jun Koseki; Tsuyoshi Yamamoto; Akihiro Sugawara; Hirofumi Nakano; Shuichi Hirono; Kazuro Shiomi; Takeshi Watanabe; Hisaaki Taniguchi; K Barry Sharpless; Satoshi Omura; Toshiaki Sunazuka
Journal: Proc Natl Acad Sci U S A Date: 2013-09-16 Impact factor: 11.205

Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates.

1. α-Azido ketones. Part 7: synthesis of 1,4-disubstituted triazoles by the "click" reaction of various terminal acetylenes with phenacyl azides or α-azidobenzo(hetera)cyclanones.

2. Simple and efficient synthesis of 5'-aryl-5'-deoxyguanosine analogs by azide-alkyne click reaction and their antileishmanial activities.

3. Decarboxylative Alkynylation.

4. Synthesis of a 10,000-membered library of molecules resembling carpanone and discovery of vesicular traffic inhibitors.

Review 5. Computational studies on the regioselectivity of metal-catalyzed synthesis of 1,2,3 triazoles via click reaction: a review.

6. Observation of the controlled assembly of preclick components in the in situ click chemistry generation of a chitinase inhibitor.

7. Dimeric isoxazolyl-1,4-dihydropyridines have enhanced binding at the multi-drug resistance transporter.

8. Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes.

9. Ultrasound-promoted copper-catalyzed azide-alkyne cycloaddition.

10. Copper-Catalyzed Azide-Alkyne Click Chemistry for Bioconjugation.