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Literature DB >> 24102696

Copper-mediated dehydrogenative biaryl coupling of naphthylamines and 1,3-azoles.

Riko Odani¹, Koji Hirano, Tetsuya Satoh, Masahiro Miura.

Abstract

A copper-mediated dehydrogenative biaryl cross-coupling of naphthylamines and 1,3-azoles has been developed. The key to its success is the introduction of N,N-bidentate coordination system based on the picolinamide directing group. The reaction proceeds smoothly without precious transition metal catalysts and provides highly π-extended heterobiaryls directly.

Entities: Chemical

Year: 2013 PMID： 24102696 DOI： 10.1021/jo402078q

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

7 in total

Review 1. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors: Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal: Chem Soc Rev Date: 2018-08-28 Impact factor: 54.564

2. Copper-promoted site-selective carbonylation of sp³ and sp² C-H bonds with nitromethane.

Authors: Xuesong Wu; Jinmin Miao; Yanrong Li; Guigen Li; Haibo Ge
Journal: Chem Sci Date: 2016-04-26 Impact factor: 9.825

Review 3. Synthetic Applications of Oxidative Aromatic Coupling-From Biphenols to Nanographenes.

Authors: Marek Grzybowski; Bartłomiej Sadowski; Holger Butenschön; Daniel T Gryko
Journal: Angew Chem Int Ed Engl Date: 2019-12-03 Impact factor: 15.336

4. Overcoming peri- and ortho-selectivity in C-H methylation of 1-naphthaldehydes by a tunable transient ligand strategy.

Authors: Yujian Mao; Jing Jiang; Dandan Yuan; Xiuzhen Chen; Yanan Wang; Lihong Hu; Yinan Zhang
Journal: Chem Sci Date: 2022-01-06 Impact factor: 9.825

Copper-mediated dehydrogenative biaryl coupling of naphthylamines and 1,3-azoles.

Review 1. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

2. Copper-promoted site-selective carbonylation of sp³ and sp² C-H bonds with nitromethane.

Review 3. Synthetic Applications of Oxidative Aromatic Coupling-From Biphenols to Nanographenes.

4. Overcoming peri- and ortho-selectivity in C-H methylation of 1-naphthaldehydes by a tunable transient ligand strategy.

5. Copper-catalyzed cross-dehydrogenative coupling between quinazoline-3-oxides and indoles.

6. Pyridine-enabled copper-promoted cross dehydrogenative coupling of C(sp²)-H and unactivated C(sp³)-H bonds.

7. Rh^I/Rh^III catalyst-controlled divergent aryl/heteroaryl C-H bond functionalization of picolinamides with alkynes.

Copper-mediated dehydrogenative biaryl coupling of naphthylamines and 1,3-azoles.

Review 1. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

2. Copper-promoted site-selective carbonylation of sp3 and sp2 C-H bonds with nitromethane.

Review 3. Synthetic Applications of Oxidative Aromatic Coupling-From Biphenols to Nanographenes.

4. Overcoming peri- and ortho-selectivity in C-H methylation of 1-naphthaldehydes by a tunable transient ligand strategy.

5. Copper-catalyzed cross-dehydrogenative coupling between quinazoline-3-oxides and indoles.

6. Pyridine-enabled copper-promoted cross dehydrogenative coupling of C(sp2)-H and unactivated C(sp3)-H bonds.

7. RhI/RhIII catalyst-controlled divergent aryl/heteroaryl C-H bond functionalization of picolinamides with alkynes.

2. Copper-promoted site-selective carbonylation of sp³ and sp² C-H bonds with nitromethane.

6. Pyridine-enabled copper-promoted cross dehydrogenative coupling of C(sp²)-H and unactivated C(sp³)-H bonds.

7. Rh^I/Rh^III catalyst-controlled divergent aryl/heteroaryl C-H bond functionalization of picolinamides with alkynes.