Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Silanol: a traceless directing group for Pd-catalyzed o-alkenylation of phenols.

Literature DB >> 21766826

Silanol: a traceless directing group for Pd-catalyzed o-alkenylation of phenols.

Chunhui Huang¹, Buddhadeb Chattopadhyay, Vladimir Gevorgyan.

Abstract

A silanol-directed, Pd(II)-catalyzed C-H alkenylation of phenols is reported. This work features silanol, as a novel traceless directing group, and a directed o-C-H alkenylation of phenols. This new method allows for efficient synthesis of diverse alkenylated phenols, including an estrone derivative.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2011 PMID： 21766826 PMCID： PMC3156791 DOI： 10.1021/ja204924j

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

45 in total

Review 1. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

Authors: Dino Alberico; Mark E Scott; Mark Lautens
Journal: Chem Rev Date: 2007-01 Impact factor: 60.622

Review 2. Sigma-chelation-directed C-H functionalizations using Pd(II) and Cu(II) catalysts: regioselectivity, stereoselectivity and catalytic turnover.

Authors: Jin-Quan Yu; Ramesh Giri; Xiao Chen
Journal: Org Biomol Chem Date: 2006-11-21 Impact factor: 3.876

3. Oxidative coupling of aromatic substrates with alkynes and alkenes under rhodium catalysis.

Authors: Tetsuya Satoh; Masahiro Miura
Journal: Chemistry Date: 2010-10-04 Impact factor: 5.236

Review 4. Recent advances in aryl-aryl bond formation by direct arylation.

Authors: Gerard P McGlacken; Lorraine M Bateman
Journal: Chem Soc Rev Date: 2009-05-22 Impact factor: 54.564

5. The catalytic intermolecular orthoarylation of phenols.

Authors: Robin B Bedford; Simon J Coles; Michael B Hursthouse; Michael E Limmert
Journal: Angew Chem Int Ed Engl Date: 2003-01-03 Impact factor: 15.336

6. A general strategy toward aromatic 1,2-ambiphilic synthons: palladium-catalyzed ortho-halogenation of PyDipSi-arenes.

Authors: Alexander S Dudnik; Natalia Chernyak; Chunhui Huang; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2010-11-08 Impact factor: 15.336

7. C-H bond functionalization in complex organic synthesis.

Authors: Kamil Godula; Dalibor Sames
Journal: Science Date: 2006-04-07 Impact factor: 47.728

8. Constructing multiply substituted arenes using sequential palladium(II)-catalyzed C-H olefination.

Authors: Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2010-08-16 Impact factor: 15.336

Review 9. C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents.

Authors: Egle M Beccalli; Gianluigi Broggini; Michela Martinelli; Silvia Sottocornola
Journal: Chem Rev Date: 2007-11-01 Impact factor: 60.622

Review 10. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Authors: Xiao Chen; Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

28 in total

1. Silicon-Tethered Strategies for C-H Functionalization Reactions.

Authors: Marvin Parasram; Vladimir Gevorgyan
Journal: Acc Chem Res Date: 2017-08-03 Impact factor: 22.384

2. Ligand-Accelerated ortho-C-H Olefination of Phenylacetic Acids.

Authors: Keary M Engle; Navid Dastbaravardeh; Peter S Thuy-Boun; Dong-Hui Wang; Aaron C Sather; Jin-Quan Yu
Journal: Organic Synth Date: 2015-03-12

3. Scope and Mechanistic Study of the Coupling Reaction of α, β-Unsaturated Carbonyl Compounds with Alkenes: Uncovering Electronic Effects on Alkene Insertion vs Oxidative Coupling Pathways.

Authors: Ki-Hyeok Kwon; Do W Lee; Chae S Yi
Journal: Organometallics Date: 2012-01-09 Impact factor: 3.876

Silanol: a traceless directing group for Pd-catalyzed o-alkenylation of phenols.

Review 1. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

Review 2. Sigma-chelation-directed C-H functionalizations using Pd(II) and Cu(II) catalysts: regioselectivity, stereoselectivity and catalytic turnover.

3. Oxidative coupling of aromatic substrates with alkynes and alkenes under rhodium catalysis.

Review 4. Recent advances in aryl-aryl bond formation by direct arylation.

5. The catalytic intermolecular orthoarylation of phenols.

6. A general strategy toward aromatic 1,2-ambiphilic synthons: palladium-catalyzed ortho-halogenation of PyDipSi-arenes.

7. C-H bond functionalization in complex organic synthesis.

8. Constructing multiply substituted arenes using sequential palladium(II)-catalyzed C-H olefination.

Review 9. C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents.

Review 10. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

1. Silicon-Tethered Strategies for C-H Functionalization Reactions.

2. Ligand-Accelerated ortho-C-H Olefination of Phenylacetic Acids.

3. Scope and Mechanistic Study of the Coupling Reaction of α, β-Unsaturated Carbonyl Compounds with Alkenes: Uncovering Electronic Effects on Alkene Insertion vs Oxidative Coupling Pathways.

4. Ether-directed ortho-C-H olefination with a palladium(II)/monoprotected amino acid catalyst.

5. C-H Activation: A surrogate for selectivity.

6. Meta-selective C-H functionalization using a nitrile-based directing group and cleavable Si-tether.

7. Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.

8. Pd-catalyzed modifiable silanol-directed aromatic C-H oxygenation.

9. Pd(II)-catalyzed ortho- or meta-C-H olefination of phenol derivatives.

10. Ligand-accelerated non-directed C-H functionalization of arenes.