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Literature DB >> 24180517

Copper-catalyzed etherification of arene C-H bonds.

Abstract

A method for direct, auxiliary-assisted alkoxylation and phenoxylation of β-sp(2) C-H bonds of benzoic acid derivatives and γ-sp(2) C-H bonds of amine derivatives is reported. The reaction employs (CuOH)2CO3 catalyst, air as an oxidant, phenol or alcohol coupling partner, DMF, pyridine, or DMPU solvent, and K2CO3, tetramethylguanidine, or K3PO4 base at 70-130 °C.

Entities: Chemical

Mesh：

Substances：

Year: 2013 PMID： 24180517 PMCID： PMC3880618 DOI： 10.1021/ol402904d

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

47 in total

1. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors: Dmitry Shabashov; Olafs Daugulis
Journal: J Am Chem Soc Date: 2010-03-24 Impact factor: 15.419

2. Ortho- and para-selective ruthenium-catalyzed C(sp2)-H oxygenations of phenol derivatives.

Authors: Weiping Liu; Lutz Ackermann
Journal: Org Lett Date: 2013-06-25 Impact factor: 6.005

3. Copper-catalyzed aerobic oxidative functionalization of an arene C-H bond: evidence for an aryl-copper(III) intermediate.

Authors: Amanda E King; Lauren M Huffman; Alicia Casitas; Miquel Costas; Xavi Ribas; Shannon S Stahl
Journal: J Am Chem Soc Date: 2010-09-01 Impact factor: 15.419

Review 4. High-valent organometallic copper and palladium in catalysis.

Authors: Amanda J Hickman; Melanie S Sanford
Journal: Nature Date: 2012-04-11 Impact factor: 49.962

5. β-Arylation of carboxamides via iron-catalyzed C(sp3)-H bond activation.

Authors: Rui Shang; Laurean Ilies; Arimasa Matsumoto; Eiichi Nakamura
Journal: J Am Chem Soc Date: 2013-04-16 Impact factor: 15.419

6. Nickel-catalyzed direct alkylation of C-H bonds in benzamides and acrylamides with functionalized alkyl halides via bidentate-chelation assistance.

Authors: Yoshinori Aihara; Naoto Chatani
Journal: J Am Chem Soc Date: 2013-04-01 Impact factor: 15.419

7. Copper-promoted sulfenylation of sp2 C-H bonds.

Authors: Ly Dieu Tran; Ilya Popov; Olafs Daugulis
Journal: J Am Chem Soc Date: 2012-10-29 Impact factor: 15.419

8. Synthesis of aryl ethers from benzoates through carboxylate-directed C-H-activating alkoxylation with concomitant protodecarboxylation.

Authors: Sukalyan Bhadra; Wojciech I Dzik; Lukas J Gooßen
Journal: Angew Chem Int Ed Engl Date: 2013-01-31 Impact factor: 15.336

9. Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds.

Authors: Thanh Truong; Kristine Klimovica; Olafs Daugulis
Journal: J Am Chem Soc Date: 2013-06-12 Impact factor: 15.419

10. Cu-catalyzed mild C(sp2)-H functionalization assisted by carboxylic acids en route to hydroxylated arenes.

Authors: Joan Gallardo-Donaire; Ruben Martin
Journal: J Am Chem Soc Date: 2013-06-14 Impact factor: 15.419

15 in total

1. Cobalt-catalyzed, aminoquinoline-directed C(sp²)-H bond alkenylation by alkynes.

Authors: Liene Grigorjeva; Olafs Daugulis
Journal: Angew Chem Int Ed Engl Date: 2014-07-24 Impact factor: 15.336

2. Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.

Authors: Pavel Starkov; Jared T Moore; Douglas C Duquette; Brian M Stoltz; Ilan Marek
Journal: J Am Chem Soc Date: 2017-07-07 Impact factor: 15.419

Copper-catalyzed etherification of arene C-H bonds.

1. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

2. Ortho- and para-selective ruthenium-catalyzed C(sp2)-H oxygenations of phenol derivatives.

3. Copper-catalyzed aerobic oxidative functionalization of an arene C-H bond: evidence for an aryl-copper(III) intermediate.

Review 4. High-valent organometallic copper and palladium in catalysis.

5. β-Arylation of carboxamides via iron-catalyzed C(sp3)-H bond activation.

6. Nickel-catalyzed direct alkylation of C-H bonds in benzamides and acrylamides with functionalized alkyl halides via bidentate-chelation assistance.

7. Copper-promoted sulfenylation of sp2 C-H bonds.

8. Synthesis of aryl ethers from benzoates through carboxylate-directed C-H-activating alkoxylation with concomitant protodecarboxylation.

9. Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds.

10. Cu-catalyzed mild C(sp2)-H functionalization assisted by carboxylic acids en route to hydroxylated arenes.

1. Cobalt-catalyzed, aminoquinoline-directed C(sp²)-H bond alkenylation by alkynes.

2. Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.

3. Bidentate, monoanionic auxiliary-directed functionalization of carbon-hydrogen bonds.

4. Cobalt-promoted dimerization of aminoquinoline benzamides.

5. Nickel-Catalyzed Reduction of Secondary and Tertiary Amides.

6. Nickel-Catalyzed Esterification of Aliphatic Amides.

7. Recent Advances in the C-H-Functionalization of the Distal Positions in Pyridines and Quinolines.

8. Cobalt-catalyzed direct carbonylation of aminoquinoline benzamides.

9. Cobalt-catalyzed, aminoquinoline-directed coupling of sp(2) C-H bonds with alkenes.

10. Nucleophilic C-H Etherification of Heteroarenes Enabled by Base-Catalyzed Halogen Transfer.