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Literature DB >> 27534735

Synthesis of Functionalized Dihydrobenzofurans by Direct Aryl C-O Bond Formation under Mild Conditions.

Joseph Alvarado¹, Jeremy Fournier¹, Armen Zakarian¹.

Abstract

A method for the synthesis of dihydrobenzofurans by a direct aryl C-O bond formation is described. A mechanistic pathway for the reaction, distinct from previously described similar transformations, allows for mild reaction conditions that are expected to be compatible with functionalized substrates.

Entities: Chemical Gene

Keywords: copper; cyclization; fused-ring systems; iodonium salts; oxygen heterocycles

Mesh：

Substances：

Year: 2016 PMID： 27534735 PMCID： PMC5189712 DOI： 10.1002/anie.201605648

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

25 in total

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Authors: Will R Gutekunst; Phil S Baran
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2. Observation and mechanistic study of facile C-O bond formation between a well-defined aryl-copper(III) complex and oxygen nucleophiles.

Authors: Lauren M Huffman; Alicia Casitas; Marc Font; Mercè Canta; Miquel Costas; Xavi Ribas; Shannon S Stahl
Journal: Chemistry Date: 2011-09-12 Impact factor: 5.236

3. Concise syntheses of dictyodendrins A and F by a sequential C-H functionalization strategy.

Authors: Atsushi D Yamaguchi; Kathryn M Chepiga; Junichiro Yamaguchi; Kenichiro Itami; Huw M L Davies
Journal: J Am Chem Soc Date: 2015-01-06 Impact factor: 15.419

4. Highly convergent total synthesis of (+)-lithospermic acid via a late-stage intermolecular C-H olefination.

Authors: Dong-Hui Wang; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2011-03-28 Impact factor: 15.419

5. Use of tunable ligands allows for intermolecular Pd-catalyzed C--O bond formation.

Authors: Andrei V Vorogushin; Xiaohua Huang; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2005-06-08 Impact factor: 15.419

6. Enantioselective Total Synthesis of (-)-Incarviatone A.

Authors: Benke Hong; Chao Li; Zhen Wang; Jie Chen; Houhua Li; Xiaoguang Lei
Journal: J Am Chem Soc Date: 2015-09-15 Impact factor: 15.419

7. Room temperature, metal-free synthesis of diaryl ethers with use of diaryliodonium salts.

Authors: Nazli Jalalian; Eloisa E Ishikawa; Luiz F Silva; Berit Olofsson
Journal: Org Lett Date: 2011-02-14 Impact factor: 6.005

8. 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

Synthesis of Functionalized Dihydrobenzofurans by Direct Aryl C-O Bond Formation under Mild Conditions.

1. Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation.

2. Observation and mechanistic study of facile C-O bond formation between a well-defined aryl-copper(III) complex and oxygen nucleophiles.

3. Concise syntheses of dictyodendrins A and F by a sequential C-H functionalization strategy.

4. Highly convergent total synthesis of (+)-lithospermic acid via a late-stage intermolecular C-H olefination.

5. Use of tunable ligands allows for intermolecular Pd-catalyzed C--O bond formation.

6. Enantioselective Total Synthesis of (-)-Incarviatone A.

7. Room temperature, metal-free synthesis of diaryl ethers with use of diaryliodonium salts.

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

9. Diaryliodonium salts: a journey from obscurity to fame.

10. Para-Selective Cu-Catalyzed C-H Aryloxylation of Electron-Rich Arenes and Heteroarenes.

1. Competing Pathways in O-Arylations with Diaryliodonium Salts: Mechanistic Insights.

Review 2. Recent Advances in Phthalan and Coumaran Chemistry.