Literature DB >> 31404296

Solventless and Metal-free Regioselective Hydrofluorination of Functionalized Alkynes and Allenes: An Efficient Protocol for the Synthesis of gem-Difluorides.

Zhichao Lu1, Bhvandip S Bajwa2, Shiwen Liu3, Sheye Lee2, Gerald B Hammond1, Bo Xu3.   

Abstract

The combination of two easily handled, highly acidic liquid HF complex reagents, DMPU-12HF and KHSO4-13HF, generated a highly acidic fluorination system that facilitated exclusive Markovnikov addition of HF to widely functionalized alkynes, including alkyne tethered drugs, or allenes to produce gem-difluorides with high atom economy, and with an easy workup.

Entities:  

Year:  2019        PMID： 31404296      PMCID： PMC6688647          DOI： 10.1039/c8gc03876g

Source DB:  PubMed          Journal:  Green Chem        ISSN： 1463-9262            Impact factor:   10.182


  24 in total

Review 1.  Modern synthetic methods for fluorine-substituted target molecules.

Authors:  Masaki Shimizu; Tamejiro Hiyama
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-27       Impact factor: 15.336

Review 2.  Vinflunine: discovery and synthesis of a novel microtubule inhibitor.

Authors:  Jacques Fahy; Paul Hellier; Fabienne Breillout; Christian Bailly
Journal:  Semin Oncol       Date:  2008-06       Impact factor: 4.929

3.  Ionic liquid and solid HF equivalent amine-poly(hydrogen fluoride) complexes effecting efficient environmentally friendly isobutane-isobutylene alkylation.

Authors:  George A Olah; Thomas Mathew; Alain Goeppert; Béla Török; Imre Bucsi; Xing-Ya Li; Qi Wang; Eric R Marinez; Patrice Batamack; Robert Aniszfeld; G K Surya Prakash
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

4.  Brønsted acid-promoted cyclizations of 1-siloxy-1,5-diynes.

Authors:  Jianwei Sun; Sergey A Kozmin
Journal:  J Am Chem Soc       Date:  2005-10-05       Impact factor: 15.419

5.  Intramolecular silicon-assisted cross-coupling reactions: general synthesis of medium-sized rings containing a 1,3-cis-cis diene unit.

Authors:  Scott E Denmark; Shyh-Ming Yang
Journal:  J Am Chem Soc       Date:  2002-03-13       Impact factor: 15.419

6.  Attaching the fluorine atom to organic molecules using BrF3 and other reagents directly derived from F2.

Authors:  Shlomo Rozen
Journal:  Acc Chem Res       Date:  2005-10       Impact factor: 22.384

7.  2,2-Difluoro-1,3-dimethylimidazolidine (DFI). A new fluorinating agent.

Authors:  Hidetoshi Hayashi; Hiroshi Sonoda; Kouki Fukumura; Teruyuki Nagata
Journal:  Chem Commun (Camb)       Date:  2002-08-07       Impact factor: 6.222

Review 8.  Understanding organofluorine chemistry. An introduction to the C-F bond.

Authors:  David O'Hagan
Journal:  Chem Soc Rev       Date:  2007-10-17       Impact factor: 54.564

Review 9.  Fluorine in pharmaceuticals: looking beyond intuition.

Authors:  Klaus Müller; Christoph Faeh; François Diederich
Journal:  Science       Date:  2007-09-28       Impact factor: 47.728

10.  Gem-difluorination of aminoalkynes via highly reactive dicationic species in superacid HF-SbF5: application to the efficient synthesis of difluorinated cinchona alkaloid derivatives.

Authors:  Anne-Céline Cantet; Hélène Carreyre; Jean-Pierre Gesson; Marie-Paule Jouannetaud; Brigitte Renoux
Journal:  J Org Chem       Date:  2008-03-04       Impact factor: 4.354
View more
  2 in total

1.  Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents.

Authors:  Rui Guo; Xiaotian Qi; Hengye Xiang; Paul Geaneotes; Ruihan Wang; Peng Liu; Yi-Ming Wang
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-14       Impact factor: 15.336

2.  A HF Loaded Lewis-Acidic Aluminium Chlorofluoride for Hydrofluorination Reactions.

Authors:  Maëva-Charlotte Kervarec; Erhard Kemnitz; Gudrun Scholz; Svemir Rudić; Thomas Braun; Christian Jäger; Adam A L Michalchuk; Franziska Emmerling
Journal:  Chemistry       Date:  2020-05-26       Impact factor: 5.236
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.