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Literature DB >> 30066448

Catalytic Alkyne Arylation Using Traceless Directing Groups.

Jung-Woo Park^1,2, Bubwoong Kang¹, Vy M Dong¹.

Abstract

By using Pd0 /Mandyphos, we achieved a three-component aminoarylation of alkynes to generate enamines, which are then hydrolyzed to either α-arylphenones or α,α-diarylketones. This Pd-catalyzed method overcomes established known pathways to enable the use of amines as traceless directing groups for C-C bond formation.

Entities: Chemical Disease

Keywords: alkynes; aminoarylation; multicomponent coupling; palladium; regiocontrol

Mesh：

Substances：
Alkynes
Palladium

Year: 2018 PMID： 30066448 PMCID： PMC6661160 DOI： 10.1002/anie.201804955

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

43 in total

1. The catalytic hydroamination of alkynes.

Authors: Frauke Pohlki; Sven Doye
Journal: Chem Soc Rev Date: 2003-03 Impact factor: 54.564

2. Brønsted Acid-Mediated Hydrative Arylation of Unactivated Alkynes.

Authors: Daniel Kaiser; Luís F Veiros; Nuno Maulide
Journal: Chemistry Date: 2016-02-25 Impact factor: 5.236

3. A fluorobenzene adduct of Ti(IV), and catalytic carboamination to prepare alpha,beta-unsaturated imines and triaryl-substituted quinolines.

Authors: Falguni Basuli; Halikhedkar Aneetha; John C Huffman; Daniel J Mindiola
Journal: J Am Chem Soc Date: 2005-12-28 Impact factor: 15.419

4. Bis(amidate)bis(amido) titanium complex: a regioselective intermolecular alkyne hydroamination catalyst.

Authors: Jacky C-H Yim; Jason A Bexrud; Rashidat O Ayinla; David C Leitch; Laurel L Schafer
Journal: J Org Chem Date: 2014-02-21 Impact factor: 4.354

5. A decarboxylative approach for regioselective hydroarylation of alkynes.

Authors: Jing Zhang; Ruja Shrestha; John F Hartwig; Pinjing Zhao
Journal: Nat Chem Date: 2016-09-05 Impact factor: 24.427

6. Cobalt(iii) catalyzed C-8 selective C-H and C-O coupling of quinoline N-oxide with internal alkynes via C-H activation and oxygen atom transfer.

Authors: Nagaraju Barsu; Malay Sen; J Richard Premkumar; Basker Sundararaju
Journal: Chem Commun (Camb) Date: 2016-01-25 Impact factor: 6.222

Review 7. Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.

Authors: Richard I McDonald; Guosheng Liu; Shannon S Stahl
Journal: Chem Rev Date: 2011-03-23 Impact factor: 60.622

Catalytic Alkyne Arylation Using Traceless Directing Groups.

1. The catalytic hydroamination of alkynes.

2. Brønsted Acid-Mediated Hydrative Arylation of Unactivated Alkynes.

3. A fluorobenzene adduct of Ti(IV), and catalytic carboamination to prepare alpha,beta-unsaturated imines and triaryl-substituted quinolines.

4. Bis(amidate)bis(amido) titanium complex: a regioselective intermolecular alkyne hydroamination catalyst.

5. A decarboxylative approach for regioselective hydroarylation of alkynes.

6. Cobalt(iii) catalyzed C-8 selective C-H and C-O coupling of quinoline N-oxide with internal alkynes via C-H activation and oxygen atom transfer.

Review 7. Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.

8. Synthesis of heterocycles via palladium pi-olefin and pi-alkyne chemistry.

Review 9. Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

10. Catalytic formal [2+2+1] synthesis of pyrroles from alkynes and diazenes via Ti(II)/Ti(IV) redox catalysis.

1. A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes.