Skip to main content
Top
Published in: Topics in Catalysis 8/2017

28-04-2017 | Original Paper

Stereoselective Carboperfluoroalkylation of Internal Alkynes: Mechanistic Insights

Authors: Zhaodong Li, Estíbaliz Merino, Cristina Nevado

Published in: Topics in Catalysis | Issue 8/2017

Log in

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

A Pd-catalyzed difunctionalization of internal alkynes combining boronic acids and perfluoroalkyl iodides under mild conditions is described here. Tetrasubstituted olefins containing perfluoroalkyl groups are synthesized in high yields in a regio- and stereoselective manner. Mechanistic studies have been carried out to shed light on the nature of the likely intermediates involved in these transformations.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literature
5.
6.
go back to reference Barata-Vallejo S, Bonesi SM, Postigo A (2015) Org Biomol Chem 13:11153–11183CrossRef Barata-Vallejo S, Bonesi SM, Postigo A (2015) Org Biomol Chem 13:11153–11183CrossRef
7.
go back to reference Tamai T, Nomoto A, Tsuchii K, Minamida Y, Mitamura T, Sonoda M, Ogawa A (2012) Tetrahedron 68:10516–10522CrossRef Tamai T, Nomoto A, Tsuchii K, Minamida Y, Mitamura T, Sonoda M, Ogawa A (2012) Tetrahedron 68:10516–10522CrossRef
9.
go back to reference Li Z, García-Domínguez A, Nevado C (2015) J Am Chem Soc 137:11610–11613CrossRef Li Z, García-Domínguez A, Nevado C (2015) J Am Chem Soc 137:11610–11613CrossRef
10.
go back to reference He Y-T, Wang Q, Li L-H, Liu X-Y, Xu P-F, Liang Y-M (2015) Org Lett 17:5188–5191CrossRef He Y-T, Wang Q, Li L-H, Liu X-Y, Xu P-F, Liang Y-M (2015) Org Lett 17:5188–5191CrossRef
11.
go back to reference Wang Q, He Y-T, Zhao J-H, Qiu Y-F, Zheng L, Hu J-Y, Yang Y-C, Liu X-Y, Liang Y-M (2016) Org Lett 18:2664–2667CrossRef Wang Q, He Y-T, Zhao J-H, Qiu Y-F, Zheng L, Hu J-Y, Yang Y-C, Liu X-Y, Liang Y-M (2016) Org Lett 18:2664–2667CrossRef
14.
15.
16.
go back to reference Konno T, Daitoh T, Noiri A, Chae J, Ishihara T, Yamanaka H (2005) Tetrahedron 61:9391–9404CrossRef Konno T, Daitoh T, Noiri A, Chae J, Ishihara T, Yamanaka H (2005) Tetrahedron 61:9391–9404CrossRef
17.
go back to reference Konno T, Kinugawa R, Ishihara T, Yamada S (2014) Org Biomol Chem 12:1611–1617CrossRef Konno T, Kinugawa R, Ishihara T, Yamada S (2014) Org Biomol Chem 12:1611–1617CrossRef
18.
go back to reference Konno T, Kinugawa R, Morigaki A, Ishihara T (2009) J Org Chem 74:8456–8459CrossRef Konno T, Kinugawa R, Morigaki A, Ishihara T (2009) J Org Chem 74:8456–8459CrossRef
19.
20.
21.
go back to reference Gao P, Shen Y-W, Fang R, Hao X-H, Qiu Z-H, Yang F, Yan X-B, Wang Q, Gong X-J, Liu X-Y, Liang Y-M (2014) Angew Chem Int Ed 53:7629–7633CrossRef Gao P, Shen Y-W, Fang R, Hao X-H, Qiu Z-H, Yang F, Yan X-B, Wang Q, Gong X-J, Liu X-Y, Liang Y-M (2014) Angew Chem Int Ed 53:7629–7633CrossRef
23.
go back to reference Xu J, Wang Y-L, Gong T-J, Xiao B, Fu Y (2014) Chem Commun (Camb) 50:12915–12918CrossRef Xu J, Wang Y-L, Gong T-J, Xiao B, Fu Y (2014) Chem Commun (Camb) 50:12915–12918CrossRef
24.
25.
go back to reference Hua H-L, He Y-T, Qiu Y-F, Li Y-X, Song B, Gao P, Song X-R, Guo D-H, Liu X-Y, Liang Y-M (2015) Chemistry 21:1468–1473.CrossRef Hua H-L, He Y-T, Qiu Y-F, Li Y-X, Song B, Gao P, Song X-R, Guo D-H, Liu X-Y, Liang Y-M (2015) Chemistry 21:1468–1473.CrossRef
27.
go back to reference Fuentes N, Kong W, Fernández-Sánchez L, Merino E, Nevado C (2015) J Am Chem Soc 137:964–973CrossRef Fuentes N, Kong W, Fernández-Sánchez L, Merino E, Nevado C (2015) J Am Chem Soc 137:964–973CrossRef
28.
go back to reference Kong W, Casimiro M, Fuentes N, Merino E, Nevado C (2013) Angew Chem Int Ed 52:13086–13090CrossRef Kong W, Casimiro M, Fuentes N, Merino E, Nevado C (2013) Angew Chem Int Ed 52:13086–13090CrossRef
29.
go back to reference Kong W, Casimiro M, Merino E, Nevado C (2013) J Am Chem Soc 135:14480–14483CrossRef Kong W, Casimiro M, Merino E, Nevado C (2013) J Am Chem Soc 135:14480–14483CrossRef
30.
go back to reference Kong W, Feige P, de Haro T, Nevado C (2013) Angew Chem Int Ed 52:2469–2473CrossRef Kong W, Feige P, de Haro T, Nevado C (2013) Angew Chem Int Ed 52:2469–2473CrossRef
31.
go back to reference Kong W, Fuentes N, García-Domínguez A, Merino E, Nevado C (2015) Angew Chem Int Ed 54:2487–2491CrossRef Kong W, Fuentes N, García-Domínguez A, Merino E, Nevado C (2015) Angew Chem Int Ed 54:2487–2491CrossRef
32.
go back to reference Kong W, Merino E, Nevado C (2014) Angew Chem Int Ed 53:5078–5082 Kong W, Merino E, Nevado C (2014) Angew Chem Int Ed 53:5078–5082
33.
go back to reference Chen Q-Y, Yang Z-Y, Zhao C-X, Qiu Z-M (1988) J Chem Soc Perkin Trans 1:563–567.CrossRef Chen Q-Y, Yang Z-Y, Zhao C-X, Qiu Z-M (1988) J Chem Soc Perkin Trans 1:563–567.CrossRef
34.
go back to reference Feng Z, Min Q-Q, Zhao H-Y, Gu J-W, Zhang X (2015) Angew Chem Int Ed 54:1270–1274CrossRef Feng Z, Min Q-Q, Zhao H-Y, Gu J-W, Zhang X (2015) Angew Chem Int Ed 54:1270–1274CrossRef
35.
36.
go back to reference Qingyun C, Zhenyu Y (1985) Acta Chim Sin 43:1118–1120. Qingyun C, Zhenyu Y (1985) Acta Chim Sin 43:1118–1120.
37.
go back to reference Galli C, Guarnieri A, Koch H, Mencarelli P, Rappoport Z (1997) J Org Chem 62:4072–4077CrossRef Galli C, Guarnieri A, Koch H, Mencarelli P, Rappoport Z (1997) J Org Chem 62:4072–4077CrossRef
Metadata
Title
Stereoselective Carboperfluoroalkylation of Internal Alkynes: Mechanistic Insights
Authors
Zhaodong Li
Estíbaliz Merino
Cristina Nevado
Publication date
28-04-2017
Publisher
Springer US
Published in
Topics in Catalysis / Issue 8/2017
Print ISSN: 1022-5528
Electronic ISSN: 1572-9028
DOI
https://doi.org/10.1007/s11244-017-0743-y

Other articles of this Issue 8/2017

Topics in Catalysis 8/2017 Go to the issue

Preface

Preface

Premium Partners