Literature DB >> 29624064

Metal-Free and User-Friendly Regioselective Hydroxyfluorination of Olefins.

Daniel M Sedgwick1,2, Inés López1, Raquel Román2, Nanako Kobayashi3, Otome E Okoromoba4, Bo Xu5, Gerald B Hammond4, Pablo Barrio1, Santos Fustero1,2.   

Abstract

A simple, user-friendly, metal-free protocol for the regioselective anti-Markovnikov hydrofluorination of olefins using readily available and inexpensive reagents has been developed. This new approach displays a broader scope than previously reported methodologies and has been applied to the late-stage fluorination of a complex molecule, giving rise to a fluorosteroid derivative. The stereochemistry of the process has also been studied in some detail.

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Year:  2018        PMID： 29624064      PMCID： PMC6237092          DOI： 10.1021/acs.orglett.8b00681

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  24 in total

Review 1.  Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II-III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas.

Authors:  Yu Zhou; Jiang Wang; Zhanni Gu; Shuni Wang; Wei Zhu; José Luis Aceña; Vadim A Soloshonok; Kunisuke Izawa; Hong Liu
Journal:  Chem Rev       Date:  2016-01-12       Impact factor: 60.622

2.  A doubly axially chiral phosphoric acid catalyst for the asymmetric tandem oxyfluorination of enamides.

Authors:  Takashi Honjo; Robert J Phipps; Vivek Rauniyar; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-29       Impact factor: 15.336

3.  Hypervalent Iodine/HF Reagents for the Synthesis of 3-Fluoropyrrolidines.

Authors:  Tsugio Kitamura; Azusa Miyake; Kensuke Muta; And Juzo Oyamada
Journal:  J Org Chem       Date:  2017-07-11       Impact factor: 4.354

4.  Diastereodivergent hydroxyfluorination of cyclic and acyclic allylic amines: synthesis of 4-deoxy-4-fluorophytosphingosines.

Authors:  Alexander J Cresswell; Stephen G Davies; James A Lee; Melloney J Morris; Paul M Roberts; James E Thomson
Journal:  J Org Chem       Date:  2012-08-13       Impact factor: 4.354

5.  Pd-Catalyzed Regioselective 1,2-Difunctionalization of Vinylarenes with Alkenyl Triflates and Aryl Boronic Acids at Ambient Temperature.

Authors:  Zhijie Kuang; Kai Yang; Qiuling Song
Journal:  Org Lett       Date:  2017-05-11       Impact factor: 6.005

6.  Iron-Catalyzed Intermolecular 1,2-Difunctionalization of Styrenes and Conjugated Alkenes with Silanes and Nucleophiles.

Authors:  Yuan Yang; Ren-Jie Song; Xuan-Hui Ouyang; Cheng-Yong Wang; Jin-Heng Li; Shenglian Luo
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-29       Impact factor: 15.336

7.  Pd-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Unactivated Olefins by a Heck Reaction/Enolate Cyclization Cascade.

Authors:  Roshan K Dhungana; Bijay Shrestha; Rajani Thapa-Magar; Prakash Basnet; Ramesh Giri
Journal:  Org Lett       Date:  2017-04-06       Impact factor: 6.005

8.  Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions.

Authors:  Otome E Okoromoba; Zhou Li; Nicole Robertson; Mark S Mashuta; Uenifer R Couto; Cláudio F Tormena; Bo Xu; Gerald B Hammond
Journal:  Chem Commun (Camb)       Date:  2016-11-08       Impact factor: 6.222

Review 9.  Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors:  Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal:  Chem Rev       Date:  2013-12-03       Impact factor: 60.622

10.  Searching for new reactivity (Nobel lecture).

Authors:  K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2002-06-17       Impact factor: 15.336
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  2 in total

1.  Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.

Authors:  Sota Akiyama; Koji Kubota; Malte S Mikus; Paulo H S Paioti; Filippo Romiti; Qinghe Liu; Yuebiao Zhou; Amir H Hoveyda; Hajime Ito
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-16       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

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