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Literature DB >> 23161862

Sustainable synthesis of diverse privileged heterocycles by palladium-catalyzed aerobic oxidative isocyanide insertion.

Tjøstil Vlaar¹, Razvan C Cioc, Pieter Mampuys, Bert U W Maes, Romano V A Orru, Eelco Ruijter.

Abstract

O(2) in, H(2)O out: Various diamines and related bisnucleophiles readily undergo oxidative isocyanide insertion with Pd(OAc)(2) (1 mol %) as the catalyst and O(2) as the terminal oxidant to give a diverse array of medicinally relevant N heterocycles. The utility of this highly sustainable method is demonstrated by a formal synthesis of the antihistamines astemizole and norastemizole.

Entities: Chemical

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Year: 2012 PMID： 23161862 DOI： 10.1002/anie.201207410

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

13 in total

1. Mechanistic Basis for Efficient, Site-Selective, Aerobic Catalytic Turnover in Pd-Catalyzed C-H Imidoylation of Heterocycle-Containing Molecules.

Authors: Stephen J Tereniak; Shannon S Stahl
Journal: J Am Chem Soc Date: 2017-10-06 Impact factor: 15.419

2. Divergent 2-Chloroquinazolin-4(3H)-one Rearrangement: Twisted-Cyclic Guanidine Formation or Ring-Fused N-Acylguanidines via a Domino Process.

Authors: Gang Yan; Bereket L Zekarias; Xiaoyu Li; Victor A Jaffett; Ilia A Guzei; Jennifer E Golden
Journal: Chemistry Date: 2020-02-06 Impact factor: 5.236

3. NHC-Ni(II)-catalyzed cyclopropene-isocyanide [5 + 1] benzannulation.

Authors: Jian-Qiang Huang; Meng Yu; Xuefeng Yong; Chun-Yu Ho
Journal: Nat Commun Date: 2022-07-16 Impact factor: 17.694

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

Authors: Suravi Chakrabarty; Shruti Choudhary; Arpit Doshi; Fa-Qiang Liu; Rishabh Mohan; Manasa P Ravindra; Dhruv Shah; Xun Yang; Fraser F Fleming
Journal: Adv Synth Catal Date: 2014-06-20 Impact factor: 5.837

5. Access to 1-amino-3,4-dihydroisoquinolines via palladium-catalyzed C-H bond aminoimidoylation reaction from functionalized isocyanides.

Authors: Zhuang Xiong; Panyuan Cai; Yingshuang Mei; Jian Wang
Journal: RSC Adv Date: 2019-12-18 Impact factor: 4.036

Sustainable synthesis of diverse privileged heterocycles by palladium-catalyzed aerobic oxidative isocyanide insertion.

1. Mechanistic Basis for Efficient, Site-Selective, Aerobic Catalytic Turnover in Pd-Catalyzed C-H Imidoylation of Heterocycle-Containing Molecules.

2. Divergent 2-Chloroquinazolin-4(3H)-one Rearrangement: Twisted-Cyclic Guanidine Formation or Ring-Fused N-Acylguanidines via a Domino Process.

3. NHC-Ni(II)-catalyzed cyclopropene-isocyanide [5 + 1] benzannulation.

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

5. Access to 1-amino-3,4-dihydroisoquinolines via palladium-catalyzed C-H bond aminoimidoylation reaction from functionalized isocyanides.

Review 6. Recent advancements on the use of 2-methyltetrahydrofuran in organometallic chemistry.

Review 7. Chemical Aspects of Human and Environmental Overload with Fluorine.

8. Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade.

9. Stereoselective Synthesis of Fused Vinylcyclopropanes by Intramolecular Tsuji-Trost Cascade Cyclization.

Review 10. Recent Advances in Palladium-Catalyzed Isocyanide Insertions.