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Literature DB >> 22059375

Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes.

Masayuki Wasa¹, Keary M Engle, David W Lin, Eun Jeong Yoo, Jin-Quan Yu.

Abstract

Systematic ligand development has led to the identification of novel mono-N-protected amino acid ligands for Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes. A diverse range of organoboron reagents can be used as coupling partners, and the reaction proceeds under mild conditions. These results provide a new retrosynthetic disconnection for the construction of enantioenriched cis-substituted cyclopropanecarboxylic acids.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2011 PMID： 22059375 PMCID： PMC3241475 DOI： 10.1021/ja207607s

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

29 in total

1. Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions.

Authors: Ramesh Giri; Xiao Chen; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2005-03-29 Impact factor: 15.336

2. Enantioselective C-H amination using cationic ruthenium(II)-pybox catalysts.

Authors: Erika Milczek; Nadège Boudet; Simon Blakey
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

3. Functionalization of organic molecules by transition-metal-catalyzed C(sp3)-H activation.

Authors: Rodolphe Jazzar; Julien Hitce; Alice Renaudat; Julien Sofack-Kreutzer; Olivier Baudoin
Journal: Chemistry Date: 2010-03-01 Impact factor: 5.236

4. Mechanism of Pd(OAc)2/DMSO-catalyzed aerobic alcohol oxidation: mass-transfer-limitation effects and catalyst decomposition pathways.

Authors: Bradley A Steinhoff; Shannon S Stahl
Journal: J Am Chem Soc Date: 2006-04-05 Impact factor: 15.419

5. Cross-coupling of C(sp)-H Bonds with Organometallic Reagents via Pd(II)/Pd(0) Catalysis**

Authors: Masayuki Wasa; Keary M Engle; Jin-Quan Yu
Journal: Isr J Chem Date: 2010-12 Impact factor: 3.333

6. Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent Suzuki reactions of racemic acylated halohydrins.

Authors: Nathan A Owston; Gregory C Fu
Journal: J Am Chem Soc Date: 2010-09-01 Impact factor: 15.419

7. Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic alpha-chloroamides.

Authors: Pamela M Lundin; Gregory C Fu
Journal: J Am Chem Soc Date: 2010-08-18 Impact factor: 15.419

8. Amide-Directed Arylation of sp C-H Bonds using Pd(II) and Pd(0) Catalysts.

Authors: Masayuki Wasa; Jin-Quan Yu
Journal: Tetrahedron Date: 2010-06-26 Impact factor: 2.457

9. Pd0/PR3-catalyzed arylation of nicotinic and isonicotinic acid derivatives.

Authors: Masayuki Wasa; Brady T Worrell; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2010-02-08 Impact factor: 15.336

10. Enantioselective alkyl-alkyl Suzuki cross-couplings of unactivated homobenzylic halides.

Authors: Bunnai Saito; Gregory C Fu
Journal: J Am Chem Soc Date: 2008-05-01 Impact factor: 15.419

51 in total

Review 1. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors: Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal: Chem Rev Date: 2015-08-13 Impact factor: 60.622

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. Palladium-Catalyzed C-H Arylation Using Aryltrifluoroborates in Conjunction with a Mn^III Oxidant under Mild Conditions.

Authors: Cydney K Seigerman; Tiffiny M Micyus; Sharon R Neufeldt; Melanie S Sanford
Journal: Tetrahedron Date: 2013-07-08 Impact factor: 2.457

Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes.

1. Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions.

2. Enantioselective C-H amination using cationic ruthenium(II)-pybox catalysts.

3. Functionalization of organic molecules by transition-metal-catalyzed C(sp3)-H activation.

4. Mechanism of Pd(OAc)2/DMSO-catalyzed aerobic alcohol oxidation: mass-transfer-limitation effects and catalyst decomposition pathways.

5. Cross-coupling of C(sp)-H Bonds with Organometallic Reagents via Pd(II)/Pd(0) Catalysis**

6. Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent Suzuki reactions of racemic acylated halohydrins.

7. Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic alpha-chloroamides.

8. Amide-Directed Arylation of sp C-H Bonds using Pd(II) and Pd(0) Catalysts.

9. Pd0/PR3-catalyzed arylation of nicotinic and isonicotinic acid derivatives.

10. Enantioselective alkyl-alkyl Suzuki cross-couplings of unactivated homobenzylic halides.

Review 1. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

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

3. Palladium-Catalyzed C-H Arylation Using Aryltrifluoroborates in Conjunction with a Mn^III Oxidant under Mild Conditions.

4. Enantioselective γ-C(sp³)-H Activation of Alkyl Amines via Pd(II)/Pd(0) Catalysis.

5. Pd^II -Catalyzed Enantioselective C(sp³ )-H Activation/Cross-Coupling Reactions of Free Carboxylic Acids.

6. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

7. Kinetic Resolution of Benzylamines via Palladium(II)-Catalyzed C-H Cross-Coupling.

8. Ligand-enabled cross-coupling of C(sp(3))-H bonds with arylsilanes.

9. Palladium(II)-catalyzed highly enantioselective C-H arylation of cyclopropylmethylamines.

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