Literature DB >> 23957378

Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

Deepankar Das1, Daniel Seidel.   

Abstract

Redox-neutral formation of C-P bonds in the α-position of class="Chemical">amines was achieved via a class="Chemical">process that features a combination of an oxidative α-C-H bond functionalization and a reductive N-alkylation. class="Chemical">pan class="Chemical">Benzoic acid functions as an efficient catalyst in this three-component reaction of cyclic secondary amines, aldehydes and phosphine oxides to provide rapid access to α-amino phosphine oxides not easily accessible by classic Kabachnik-Fields reactions.

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Year:  2013        PMID: 23957378      PMCID: PMC3818705          DOI: 10.1021/ol401858k

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


  53 in total

1.  Product-selectivity control by the nature of the catalyst: Lewis acid-catalyzed selective formation of ring-fused tetrahydroquinolines and tetrahydroazepines via intramolecular redox reaction.

Authors:  Guanghua Zhou; Junliang Zhang
Journal:  Chem Commun (Camb)       Date:  2010-08-10       Impact factor: 6.222

2.  Alpha-amination of nitrogen heterocycles: ring-fused aminals.

Authors:  Chen Zhang; Chandra Kanta De; Rudrajit Mal; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2008-01-16       Impact factor: 15.419

3.  Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation.

Authors:  Li Cui; Longwu Ye; Liming Zhang
Journal:  Chem Commun (Camb)       Date:  2010-03-30       Impact factor: 6.222

4.  Direct α-functionalization of saturated cyclic amines.

Authors:  Emily A Mitchell; Aldo Peschiulli; Nicolas Lefevre; Lieven Meerpoel; Bert U W Maes
Journal:  Chemistry       Date:  2012-07-24       Impact factor: 5.236

5.  An efficient synthesis of a hydroxyethylamine (HEA) isostere and its α-aminophosphonate and phosphoramidate derivatives as potential anti-HIV agents.

Authors:  Asish K Bhattacharya; Kalpeshkumar C Rana; Christophe Pannecouque; Eric De Clercq
Journal:  ChemMedChem       Date:  2012-07-11       Impact factor: 3.466

6.  Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry.

Authors:  Artur Mucha; Paweł Kafarski; Łukasz Berlicki
Journal:  J Med Chem       Date:  2011-08-05       Impact factor: 7.446

Review 7.  Recent synthesis of aminophosphonic acids as potential biological importance.

Authors:  Emilia D Naydenova; Petar T Todorov; Kolio D Troev
Journal:  Amino Acids       Date:  2009-02-20       Impact factor: 3.520

8.  Highly efficient visible-light-induced aerobic oxidative C-C, C-P coupling from C-H bonds catalyzed by a gold(III)-complex.

Authors:  Qicai Xue; Jin Xie; Hongming Jin; Yixiang Cheng; Chengjian Zhu
Journal:  Org Biomol Chem       Date:  2013-02-13       Impact factor: 3.876

9.  Lewis acid catalyzed formation of tetrahydroquinolines via an intramolecular redox process.

Authors:  Sandip Murarka; Chen Zhang; Marlena D Konieczynska; Daniel Seidel
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

10.  Nontraditional reactions of azomethine ylides: decarboxylative three-component couplings of alpha-amino acids.

Authors:  Chen Zhang; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

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  16 in total

1.  C-H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds.

Authors:  YoungKu Kang; Matthew T Richers; Conrad H Sawicki; Daniel Seidel
Journal:  Chem Commun (Camb)       Date:  2015-07-07       Impact factor: 6.222

2.  The Rügheimer-Burrows reaction revisited: Facile preparation of 4-alkylisoquinolines and 3,5-dialkylpyridines from (partially) saturated amines.

Authors:  Alena Yu Platonova; Daniel Seidel
Journal:  Tetrahedron Lett       Date:  2015-06       Impact factor: 2.415

3.  Condensation-Based Methods for the C-H Bond Functionalization of Amines.

Authors:  Weijie Chen; Daniel Seidel
Journal:  Synthesis (Stuttg)       Date:  2021-09-02       Impact factor: 3.157

4.  Redox-neutral α-arylation of amines.

Authors:  Weijie Chen; Richard G Wilde; Daniel Seidel
Journal:  Org Lett       Date:  2013-12-13       Impact factor: 6.005

5.  Intramolecular Redox-Mannich Reactions: Facile Access to the Tetrahydroprotoberberine Core.

Authors:  Longle Ma; Daniel Seidel
Journal:  Chemistry       Date:  2015-07-28       Impact factor: 5.236

6.  Redox-neutral α,β-difunctionalization of cyclic amines.

Authors:  Weijie Chen; YoungKu Kang; Richard G Wilde; Daniel Seidel
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-01       Impact factor: 15.336

7.  Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates.

Authors:  Zhengbo Zhu; Hemant S Chandak; Daniel Seidel
Journal:  Org Lett       Date:  2018-06-25       Impact factor: 6.005

8.  Dual C-H functionalization of N-aryl amines: synthesis of polycyclic amines via an oxidative Povarov approach.

Authors:  Chang Min; Abbas Sanchawala; Daniel Seidel
Journal:  Org Lett       Date:  2014-05-01       Impact factor: 6.005

9.  The redox-Mannich reaction.

Authors:  Weijie Chen; Daniel Seidel
Journal:  Org Lett       Date:  2014-05-23       Impact factor: 6.005

10.  Intramolecular [3 + 2]-cycloadditions of azomethine ylides derived from secondary amines via redox-neutral C-H functionalization.

Authors:  Kempegowda Mantelingu; Yingfu Lin; Daniel Seidel
Journal:  Org Lett       Date:  2014-11-03       Impact factor: 6.005

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