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Literature DB >> 21766839

Direct transformation of N,N-dimethylformamide to -CN: Pd-catalyzed cyanation of heteroarenes via C-H functionalization.

Abstract

This paper describes the direct cyanation of indoles and benzofurans employing N,N-dimethylformamide (DMF) as both reagent and solvent. Isotopic labeling experiments indicated that both the N and the C of the cyano group derived from DMF. This transformation offers an alternative method for preparing aryl nitriles, though it is currently limited in scope to indoles and benzofurans.

Entities: Chemical

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Year: 2011 PMID： 21766839 DOI： 10.1021/ja204063z

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

8 in total

Review 1. Recent advances in theoretical studies on transition-metal-catalyzed regioselective C-H functionalization of indoles.

Authors: Hongsheng Ma; Tongyan Yu; Longxiao Chi; Cong Huang; Xuwen Li; Rui Zhang; Chao Deng
Journal: J Mol Model Date: 2022-08-22 Impact factor: 2.172

2. One-pot regioselective C-H activation iodination-cyanation of 2,4-diarylquinazolines using malononitrile as a cyano source.

Authors: Ziqiao Yan; Banlai Ouyang; Xunchun Mao; Wei Gao; Zhihong Deng; Yiyuan Peng
Journal: RSC Adv Date: 2019-06-11 Impact factor: 4.036

3. Mechanistic Investigations of Cu-Catalyzed Fluorination of Diaryliodonium Salts: Elaborating the Cu^I/Cu^III Manifold in Copper Catalysis.

Authors: Naoko Ichiishi; Allan J Canty; Brian F Yates; Melanie S Sanford
Journal: Organometallics Date: 2014-09-22 Impact factor: 3.876

4. Solid-state Reaction of Azolium Hydrohalogen Salts with Silver Dicyanamide--Unexpected Formation of Cyanoguanidine-azoles, Reaction Mechanism and Their Hypergolic Properties.

Authors: Wei Liu; Qiu-han Lin; Yu-chuan Li; Peng-wan Chen; Tao Fang; Ru-bo Zhang; Si-ping Pang
Journal: Sci Rep Date: 2015-06-03 Impact factor: 4.379

Direct transformation of N,N-dimethylformamide to -CN: Pd-catalyzed cyanation of heteroarenes via C-H functionalization.

Review 1. Recent advances in theoretical studies on transition-metal-catalyzed regioselective C-H functionalization of indoles.

2. One-pot regioselective C-H activation iodination-cyanation of 2,4-diarylquinazolines using malononitrile as a cyano source.

3. Mechanistic Investigations of Cu-Catalyzed Fluorination of Diaryliodonium Salts: Elaborating the Cu^I/Cu^III Manifold in Copper Catalysis.

4. Solid-state Reaction of Azolium Hydrohalogen Salts with Silver Dicyanamide--Unexpected Formation of Cyanoguanidine-azoles, Reaction Mechanism and Their Hypergolic Properties.

5. Metal-Free Direct C-H Cyanation of Alkenes.

6. Improved Schmidt Conversion of Aldehydes to Nitriles Using Azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-propanol.

Review 7. Beyond a solvent: triple roles of dimethylformamide in organic chemistry.

8. Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines.

Direct transformation of N,N-dimethylformamide to -CN: Pd-catalyzed cyanation of heteroarenes via C-H functionalization.

Review 1. Recent advances in theoretical studies on transition-metal-catalyzed regioselective C-H functionalization of indoles.

2. One-pot regioselective C-H activation iodination-cyanation of 2,4-diarylquinazolines using malononitrile as a cyano source.

3. Mechanistic Investigations of Cu-Catalyzed Fluorination of Diaryliodonium Salts: Elaborating the CuI/CuIII Manifold in Copper Catalysis.

4. Solid-state Reaction of Azolium Hydrohalogen Salts with Silver Dicyanamide--Unexpected Formation of Cyanoguanidine-azoles, Reaction Mechanism and Their Hypergolic Properties.

5. Metal-Free Direct C-H Cyanation of Alkenes.

6. Improved Schmidt Conversion of Aldehydes to Nitriles Using Azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-propanol.

Review 7. Beyond a solvent: triple roles of dimethylformamide in organic chemistry.

8. Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines.

3. Mechanistic Investigations of Cu-Catalyzed Fluorination of Diaryliodonium Salts: Elaborating the Cu^I/Cu^III Manifold in Copper Catalysis.