Literature DB >> 25484847

Catalytic Isonitrile Insertions and Condensations Initiated by RNC-X Complexation.

Suravi Chakrabarty1, Shruti Choudhary1, Arpit Doshi1, Fa-Qiang Liu1, Rishabh Mohan1, Manasa P Ravindra1, Dhruv Shah1, Xun Yang2, Fraser F Fleming2.   

Abstract

Isonitriles are delicately poised chemical entities capable of being coaxed to react as nucleophiles or electrophiles. Directing this tunable reactivity with metal and non-metal catalysts provides rapid access to a large array of complex nitrogenous structures ideally functionalized for medicinal applications. Isonitrile insertion into transition metal complexes has featured in numerous synthetic and mechanistic studies, leading to rapid deployment of isonitriles in numerous catalytic processes, including multicomponent reactions (MCR). Covering the literature from 1990-2014, the present review collates reaction types to highlight reactivity trends and allow catalyst comparison.

Entities:  

Keywords:  catalysis; condensation; coupling; isocyanides; isonitriles

Year:  2014        PMID: 25484847      PMCID: PMC4251577          DOI: 10.1002/adsc.201400017

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN: 1615-4150            Impact factor:   5.837


  98 in total

1.  A Palladium-Catalyzed Synthesis of Amidines from Aryl Halides This research was supported by AstraZeneca plc.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-11-17       Impact factor: 15.336

2.  A Nickel(0)-Catalyzed Process for the Transformation of Enynes to Bicyclic Cyclopentenones.

Authors:  Minghui Zhang; Stephen L. Buchwald
Journal:  J Org Chem       Date:  1996-07-12       Impact factor: 4.354

3.  Mechanistic exploration of the palladium-catalyzed process for the synthesis of benzoxazoles and benzothiazoles.

Authors:  Valentin N Bochatay; Patrick J Boissarie; John A Murphy; Colin J Suckling; Stuart Lang
Journal:  J Org Chem       Date:  2013-01-25       Impact factor: 4.354

4.  Multicomponent synthesis of 2-imidazolines.

Authors:  Robin S Bon; Bart van Vliet; Nanda E Sprenkels; Rob F Schmitz; Frans J J de Kanter; Christian V Stevens; Marcel Swart; F Matthias Bickelhaupt; Marinus B Groen; Romano V A Orru
Journal:  J Org Chem       Date:  2005-04-29       Impact factor: 4.354

5.  A powerful palladium-catalyzed multicomponent process for the preparation of oxazolines and benzoxazoles.

Authors:  Patrick J Boissarie; Zoë E Hamilton; Stuart Lang; John A Murphy; Colin J Suckling
Journal:  Org Lett       Date:  2011-11-02       Impact factor: 6.005

6.  Organocatalytic stereocontrolled synthesis of 3,3'-pyrrolidinyl spirooxindoles by [3+2] annulation of isocyanoesters with methyleneindolinones.

Authors:  Liang-Liang Wang; Jian-Fei Bai; Lin Peng; Liang-Wen Qi; Li-Na Jia; Yun-Long Guo; Xi-Ya Luo; Xiao-Ying Xu; Li-Xin Wang
Journal:  Chem Commun (Camb)       Date:  2012-04-19       Impact factor: 6.222

7.  Synthesis of 2,5-bis(hetero)aryl 4'-substituted 4,5'-bisoxazoles via copper(I)-catalyzed domino reactions of activated methylene isocyanides with 2-phenyl- and 2-(2-thienyl)-4-[(aryl/heteroaryl)(methylthio)methylene]oxazol-5(4H)-ones.

Authors:  Somaraju Yugandar; Anand Acharya; Hiriyakkanavar Ila
Journal:  J Org Chem       Date:  2013-03-25       Impact factor: 4.354

8.  Reactions of ortho-lithiophenyl (-hetaryl) isocyanides with carbonyl compounds: rearrangements of 2-metalated 4H-3,1-benzoxazines.

Authors:  Alexander V Lygin; Armin de Meijere
Journal:  J Org Chem       Date:  2009-06-19       Impact factor: 4.354

9.  A multicomponent coupling sequence for direct access to substituted quinolines.

Authors:  Supriyo Majumder; Kevin R Gipson; Aaron L Odom
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

10.  A resource-efficient and highly flexible procedure for a three-component synthesis of 2-imidazolines.

Authors:  Niels Elders; Rob F Schmitz; Frans J J de Kanter; Eelco Ruijter; Marinus B Groen; Romano V A Orru
Journal:  J Org Chem       Date:  2007-07-12       Impact factor: 4.354

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  10 in total

1.  Direct Conversion of Nitriles into Alkene "Isonitriles".

Authors:  Yajun Li; Fraser F Fleming
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-25       Impact factor: 15.336

2.  Alkenyl Isocyanide Conjugate Additions: A Rapid Route to γ-Carbolines.

Authors:  Sergiy V Chepyshev; J Armando Lujan-Montelongo; Allen Chao; Fraser F Fleming
Journal:  Angew Chem Int Ed Engl       Date:  2017-03-13       Impact factor: 15.336

3.  Aerobic Oxidation Reactivity of Well-Defined Cobalt(II) and Cobalt(III) Aminophenol Complexes.

Authors:  Jiaqi Liu; Shannen C Lorraine; Brian S Dolinar; Jessica M Hoover
Journal:  Inorg Chem       Date:  2022-04-12       Impact factor: 5.436

4.  Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs.

Authors:  J Armando Lujan-Montelongo; Angel Ojeda Estevez; Fraser F Fleming
Journal:  European J Org Chem       Date:  2015-03

5.  Asmic: An Exceptional Building Block for Isocyanide Alkylations.

Authors:  Embarek Alwedi; J Armando Lujan-Montelongo; Bhaskar R Pitta; Allen Chao; Rodrigo Cortés-Mejía; Jorge M Del Campo; Fraser F Fleming
Journal:  Org Lett       Date:  2018-09-06       Impact factor: 6.005

6.  Enantioselective synthesis of (-)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction.

Authors:  Allegra Franchino; Pavol Jakubec; Darren J Dixon
Journal:  Org Biomol Chem       Date:  2016-01-07       Impact factor: 3.876

7.  Amino-isocyanoacridines: Novel, Tunable Solvatochromic Fluorophores as Physiological pH Probes.

Authors:  Miklós Nagy; Dávid Rácz; Zsolt László Nagy; Péter Pál Fehér; Sándor Lajos Kovács; Csaba Bankó; Zsolt Bacsó; Alexandra Kiss; Miklós Zsuga; Sándor Kéki
Journal:  Sci Rep       Date:  2019-06-03       Impact factor: 4.379

8.  Chromatography-Free Multicomponent Synthesis of Thioureas Enabled by Aqueous Solution of Elemental Sulfur.

Authors:  András Gy Németh; Renáta Szabó; Attila Domján; György M Keserű; Péter Ábrányi-Balogh
Journal:  ChemistryOpen       Date:  2020-12-30       Impact factor: 2.630

9.  Design and Synthesis of Dipeptidomimetic Isocyanonaphthalene as Enhanced-Fluorescent Chemodosimeter for Sensing Mercury Ion and Living Cells.

Authors:  Xiao-Juan Wang; Gao-Wei Li; Yi-Peng Cheng; Qiu-Ling Sun; Yuan-Qiang Hao; Chen-Hong Wang; Lan-Tao Liu
Journal:  Front Chem       Date:  2022-03-04       Impact factor: 5.221

10.  Transition-metal and oxidant-free approach for the synthesis of diverse N-heterocycles by TMSCl activation of isocyanides.

Authors:  Liangliang Luo; Hongyan Li; Jinxin Liu; Yuan Zhou; Lin Dong; You-Cai Xiao; Fen-Er Chen
Journal:  RSC Adv       Date:  2020-08-07       Impact factor: 3.361

  10 in total

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