Literature DB >> 22860624

Fe(III)/NaBH4-mediated free radical hydrofluorination of unactivated alkenes.

Timothy J Barker1, Dale L Boger.   

Abstract

A powerful Fe(III)/NaBH(4)-mediated free radical hydrofluorination of unactivated alkenes is disclosed using Selectfluor reagent as a source of fluorine and resulting in exclusive Markovnikov addition. In contrast to the traditional and unmanageable free radical hydrofluorination of alkenes, the Fe(III)/NaBH(4)-mediated reaction is conducted under exceptionally mild reaction conditions (0 °C, 5 min, CH(3)CN/H(2)O). The reaction can be conducted open to the air and with water as a cosolvent and demonstrates an outstanding substrate scope and functional group tolerance.

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Year:  2012        PMID： 22860624      PMCID： PMC3425717          DOI： 10.1021/ja3063716

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


  28 in total

1.  Radiosynthesis and evaluation of [18F]Selectfluor bis(triflate).

Authors:  Harriet Teare; Edward G Robins; Anna Kirjavainen; Sarita Forsback; Graham Sandford; Olof Solin; Sajinder K Luthra; Véronique Gouverneur
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-10       Impact factor: 15.336

2.  Synthesis of aryl fluorides on a solid support and in solution by utilizing a fluorinated solvent.

Authors:  Marion Döbele; Sylvia Vanderheiden; Nicole Jung; Stefan Bräse
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-09       Impact factor: 15.336

3.  Intermolecular Ritter-type C-H amination of unactivated sp3 carbons.

Authors:  Quentin Michaudel; Damien Thevenet; Phil S Baran
Journal:  J Am Chem Soc       Date:  2012-01-27       Impact factor: 15.419

Review 4.  Selectfluor: mechanistic insight and applications.

Authors:  Paul T Nyffeler; Sergio Gonzalez Durón; Michael D Burkart; Stéphane P Vincent; Chi-Huey Wong
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-27       Impact factor: 15.336

5.  Palladium(II)-catalyzed selective monofluorination of benzoic acids using a practical auxiliary: a weak-coordination approach.

Authors:  Kelvin S L Chan; Masayuki Wasa; Xisheng Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-11       Impact factor: 15.336

6.  Hydrazines and azides via the metal-catalyzed hydrohydrazination and hydroazidation of olefins.

Authors:  Jérôme Waser; Boris Gaspar; Hisanori Nambu; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2006-09-06       Impact factor: 15.419

7.  Cobalt-catalyzed hydroazidation of olefins: convenient access to alkyl azides.

Authors:  Jérôme Waser; Hisanori Nambu; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

8.  Total synthesis of vinblastine, vincristine, related natural products, and key structural analogues.

Authors:  Hayato Ishikawa; David A Colby; Shigeki Seto; Porino Va; Annie Tam; Hiroyuki Kakei; Thomas J Rayl; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2009-04-08       Impact factor: 15.419

Review 9.  The organometallic fluorine chemistry of palladium and rhodium: studies toward aromatic fluorination.

Authors:  Vladimir V Grushin
Journal:  Acc Chem Res       Date:  2010-01-19       Impact factor: 22.384

10.  Versatile Pd(OTf)2 x 2 H2O-catalyzed ortho-fluorination using NMP as a promoter.

Authors:  Xisheng Wang; Tian-Sheng Mei; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419
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  60 in total

Review 1.  Natural Products in the "Marketplace": Interfacing Synthesis and Biology.

Authors:  Benjamin J Huffman; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2019-02-13       Impact factor: 15.419

2.  Triarylaminium Radical Cation Promoted Coupling of Catharanthine with Vindoline: Diastereospecific Synthesis of Anhydrovinblastine and Reaction Scope.

Authors:  Byron A Boon; Dale L Boger
Journal:  J Am Chem Soc       Date:  2019-09-03       Impact factor: 15.419

3.  Ultrapotent vinblastines in which added molecular complexity further disrupts the target tubulin dimer-dimer interface.

Authors:  Daniel W Carney; John C Lukesh; Daniel M Brody; Manuela M Brütsch; Dale L Boger
Journal:  Proc Natl Acad Sci U S A       Date:  2016-08-10       Impact factor: 11.205

4.  Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion.

Authors:  Deng-Fu Lu; Cheng-Liang Zhu; Jeffrey D Sears; Hao Xu
Journal:  J Am Chem Soc       Date:  2016-08-26       Impact factor: 15.419

5.  Total synthesis and evaluation of vinblastine analogues containing systematic deep-seated modifications in the vindoline subunit ring system: core redesign.

Authors:  Kristin D Schleicher; Yoshikazu Sasaki; Annie Tam; Daisuke Kato; Katharine K Duncan; Dale L Boger
Journal:  J Med Chem       Date:  2013-01-04       Impact factor: 7.446

6.  A remarkable series of vinblastine analogues displaying enhanced activity and an unprecedented tubulin binding steric tolerance: C20' urea derivatives.

Authors:  Erick K Leggans; Katharine K Duncan; Timothy J Barker; Kristin D Schleicher; Dale L Boger
Journal:  J Med Chem       Date:  2012-12-17       Impact factor: 7.446

7.  Divergent Total Syntheses of (-)-Pseudocopsinine and (-)-Minovincinine.

Authors:  Xianhuang Zeng; Vyom Shukla; Dale L Boger
Journal:  J Org Chem       Date:  2020-11-18       Impact factor: 4.354

8.  Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.

Authors:  Steven W M Crossley; Carla Obradors; Ruben M Martinez; Ryan A Shenvi
Journal:  Chem Rev       Date:  2016-07-27       Impact factor: 60.622

9.  Vinblastine 20' Amides: Synthetic Analogues That Maintain or Improve Potency and Simultaneously Overcome Pgp-Derived Efflux and Resistance.

Authors:  John C Lukesh; Daniel W Carney; Huijun Dong; R Matthew Cross; Vyom Shukla; Katharine K Duncan; Shouliang Yang; Daniel M Brody; Manuela M Brütsch; Aleksandar Radakovic; Dale L Boger
Journal:  J Med Chem       Date:  2017-08-31       Impact factor: 7.446

10.  Strategic redox relay enables a scalable synthesis of ouabagenin, a bioactive cardenolide.

Authors:  Hans Renata; Qianghui Zhou; Phil S Baran
Journal:  Science       Date:  2013-01-04       Impact factor: 47.728
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