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Literature DB >> 18288858

Super-electron donors: bis-pyridinylidene formation by base treatment of pyridinium salts.

John A Murphy¹, Jean Garnier, Stuart R Park, Franziska Schoenebeck, Sheng-ze Zhou, Andrew T Turner.

Abstract

Deprotonation of bispyridinium salt 7b affords bispyridinylidene 10, a very powerful neutral organic two-electron donor [E1/2 (DMF)=-1.13 V vs Ag/AgCl/KCl (sat)], presumably via the pyridinylidene 8. Donor 10 reduces aryl iodides and bromides to aryl anions in excellent yield and also reductively cleaves selected phenylalkylsulfones very efficiently.

Entities: Chemical Gene Species

Mesh：

Substances：
Pyridinium Compounds

Year: 2008 PMID： 18288858 DOI： 10.1021/ol800134g

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

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Cited

16 in total

1. Studies toward the oxidative and reductive activation of C-S bonds in 2'-S-aryl-2'-thiouridine derivatives.

Authors: Ramanjaneyulu Rayala; Alain Giuglio-Tonolo; Julie Broggi; Thierry Terme; Patrice Vanelle; Patricia Theard; Maurice Médebielle; Stanislaw F Wnuk
Journal: Tetrahedron Date: 2016-04-21 Impact factor: 2.457

2. Development of an Improved System for the Carboxylation of Aryl Halides through Mechanistic Studies.

Authors: David J Charboneau; Gary W Brudvig; Nilay Hazari; Hannah M C Lant; Andrew K Saydjari
Journal: ACS Catal Date: 2019-03-14 Impact factor: 13.084

Review 3. Homogeneous Organic Electron Donors in Nickel-Catalyzed Reductive Transformations.

Authors: David J Charboneau; Nilay Hazari; Haotian Huang; Mycah R Uehling; Susan L Zultanski
Journal: J Org Chem Date: 2022-06-07 Impact factor: 4.198

4. Hybrid super electron donors - preparation and reactivity.

Authors: Jean Garnier; Douglas W Thomson; Shengze Zhou; Phillip I Jolly; Leonard E A Berlouis; John A Murphy
Journal: Beilstein J Org Chem Date: 2012-07-03 Impact factor: 2.883

5. Reductions of challenging organic substrates by a nickel complex of a noninnocent crown carbene ligand.

Authors: Neil J Findlay; Stuart R Park; Franziska Schoenebeck; Elise Cahard; Sheng-Ze Zhou; Leonard E A Berlouis; Mark D Spicer; Tell Tuttle; John A Murphy
Journal: J Am Chem Soc Date: 2010-11-10 Impact factor: 15.419

6. Overturning established chemoselectivities: selective reduction of arenes over malonates and cyanoacetates by photoactivated organic electron donors.

Authors: Eswararao Doni; Bhaskar Mondal; Steven O'Sullivan; Tell Tuttle; John A Murphy
Journal: J Am Chem Soc Date: 2013-07-19 Impact factor: 15.419

Super-electron donors: bis-pyridinylidene formation by base treatment of pyridinium salts.

1. Studies toward the oxidative and reductive activation of C-S bonds in 2'-S-aryl-2'-thiouridine derivatives.

2. Development of an Improved System for the Carboxylation of Aryl Halides through Mechanistic Studies.

Review 3. Homogeneous Organic Electron Donors in Nickel-Catalyzed Reductive Transformations.

4. Hybrid super electron donors - preparation and reactivity.

5. Reductions of challenging organic substrates by a nickel complex of a noninnocent crown carbene ligand.

6. Overturning established chemoselectivities: selective reduction of arenes over malonates and cyanoacetates by photoactivated organic electron donors.

7. Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine.

8. Amidine dications as superelectrophiles.

9. One-carbon extrusion from a tetraazafulvalene. Isolation of aldehydes and a study of their origin.

10. Pushing the limits of neutral organic electron donors: a tetra(iminophosphorano)-substituted bispyridinylidene.