Literature DB >> 34326573

Synthesis of Spirocyclic Piperidines by Radical Hydroarylation.

Racheal M Spurlin1, Amber L Harris1, Cameron J Pratt1, Nathan T Jui1.   

Abstract

Reported here are conditions for the construction of spirocyclic piperidines from linear aryl halide precursors. These conditions employ a strongly reducing organic photoredox catalyst in combination with a trialkylamine reductant to achieve formation of aryl radical species. Regioselective cyclization followed by hydrogen-atom transfer affords a range of complex spiropiperidines. This system operates efficiently under mild conditions without the need for toxic reagents or precious metals.

Entities:  

Keywords:  hydroarylation; photoredox catalysis; piperidines; radicals; spirocyclization

Year:  2020        PMID： 34326573      PMCID： PMC8318207          DOI： 10.1055/a-1315-1014

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  10 in total

Review 1.  Mu opioids and their receptors: evolution of a concept.

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Journal:  Pharmacol Rev       Date:  2013-09-27       Impact factor: 25.468

Review 2.  Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals.

Authors:  Edon Vitaku; David T Smith; Jon T Njardarson
Journal:  J Med Chem       Date:  2014-10-07       Impact factor: 7.446

3.  Organic Photoredox Catalysis.

Authors:  Nathan A Romero; David A Nicewicz
Journal:  Chem Rev       Date:  2016-06-10       Impact factor: 60.622

4.  Anti-Markovnikov Hydroarylation of Unactivated Olefins via Pyridyl Radical Intermediates.

Authors:  Allyson J Boyington; Martin-Louis Y Riu; Nathan T Jui
Journal:  J Am Chem Soc       Date:  2017-05-09       Impact factor: 15.419

5.  A Toolbox Approach To Construct Broadly Applicable Metal-Free Catalysts for Photoredox Chemistry: Deliberate Tuning of Redox Potentials and Importance of Halogens in Donor-Acceptor Cyanoarenes.

Authors:  Elisabeth Speckmeier; Tillmann G Fischer; Kirsten Zeitler
Journal:  J Am Chem Soc       Date:  2018-11-02       Impact factor: 15.419

6.  Engaging unactivated alkyl, alkenyl and aryl iodides in visible-light-mediated free radical reactions.

Authors:  John D Nguyen; Erica M D'Amato; Jagan M R Narayanam; Corey R J Stephenson
Journal:  Nat Chem       Date:  2012-10       Impact factor: 24.427

7.  Hydroarylation of Arenes via Reductive Radical-Polar Crossover.

Authors:  Autumn R Flynn; Kelly A McDaniel; Meredith E Hughes; David B Vogt; Nathan T Jui
Journal:  J Am Chem Soc       Date:  2020-05-11       Impact factor: 15.419

8.  A mild catalytic system for radical conjugate addition of nitrogen heterocycles.

Authors:  R A Aycock; H Wang; N T Jui
Journal:  Chem Sci       Date:  2017-02-13       Impact factor: 9.825

9.  A practical and scalable system for heteroaryl amino acid synthesis.

Authors:  R A Aycock; D B Vogt; N T Jui
Journal:  Chem Sci       Date:  2017-10-02       Impact factor: 9.825

Review 10.  Heterocyclic Anticancer Compounds: Recent Advances and the Paradigm Shift towards the Use of Nanomedicine's Tool Box.

Authors:  Pedro Martins; João Jesus; Sofia Santos; Luis R Raposo; Catarina Roma-Rodrigues; Pedro Viana Baptista; Alexandra R Fernandes
Journal:  Molecules       Date:  2015-09-16       Impact factor: 4.411
  10 in total
  1 in total

1.  Cathodic Radical Cyclisation of Aryl Halides Using a Strongly-Reducing Catalytic Mediator in Flow.

Authors:  Ana A Folgueiras-Amador; Alexander E Teuten; Mateo Salam-Perez; James E Pearce; Guy Denuault; Derek Pletcher; Philip J Parsons; David C Harrowven; Richard C D Brown
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-18       Impact factor: 16.823
  1 in total

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