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Literature DB >> 20187642

Pd(II)-catalyzed olefination of sp3 C-H bonds.

Masayuki Wasa¹, Keary M Engle, Jin-Quan Yu.

Abstract

The first Pd(II)-catalyzed sp(3) C-H olefination reaction has been developed using N-arylamide directing groups. Following olefination, the resulting intermediates were found to undergo rapid 1,4-addition to give the corresponding gamma-lactams. Notably, this method was effective with substrates containing alpha-hydrogen atoms and could be applied to effect methylene C-H olefination of cyclopropane substrates.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2010 PMID： 20187642 PMCID： PMC2841429 DOI： 10.1021/ja1010866

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

17 in total

1. Catalytic C-H bond functionalization with palladiumII: aerobic oxidative annulations of indoles.

Authors: Eric M Ferreira; Brian M Stoltz
Journal: J Am Chem Soc Date: 2003-08-13 Impact factor: 15.419

2. The total synthesis of (+)-dragmacidin F.

Authors: Neil K Garg; Daniel D Caspi; Brian M Stoltz
Journal: J Am Chem Soc Date: 2004-08-11 Impact factor: 15.419

3. Palladium-catalyzed intermolecular alkenylation of indoles by solvent-controlled regioselective C-H functionalization.

Authors: Neil P Grimster; Carolyn Gauntlett; Christopher R A Godfrey; Matthew J Gaunt
Journal: Angew Chem Int Ed Engl Date: 2005-05-13 Impact factor: 15.336

4. Directed palladation: fine tuning permits the catalytic 2-alkenylation of indoles.

Authors: Elena Capito; John M Brown; Alfredo Ricci
Journal: Chem Commun (Camb) Date: 2005-02-17 Impact factor: 6.222

5. 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

6. Palladium-catalyzed cross-coupling reactions in total synthesis.

Authors: K C Nicolaou; Paul G Bulger; David Sarlah
Journal: Angew Chem Int Ed Engl Date: 2005-07-18 Impact factor: 15.336

7. Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature.

Authors: Maarten D K Boele; Gino P F van Strijdonck; André H M de Vries; Paul C J Kamer; Johannes G de Vries; Piet W N M van Leeuwen
Journal: J Am Chem Soc Date: 2002-02-27 Impact factor: 15.419

8. Ligand-enabled reactivity and selectivity in a synthetically versatile aryl C-H olefination.

Authors: Dong-Hui Wang; Keary M Engle; Bing-Feng Shi; Jin-Quan Yu
Journal: Science Date: 2009-11-26 Impact factor: 47.728

9. A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole --> dihydroindoloazocine cyclization.

Authors: Phil S Baran; E J Corey
Journal: J Am Chem Soc Date: 2002-07-10 Impact factor: 15.419

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

54 in total

1. Pd(II)-catalyzed para-selective C-H arylation of monosubstituted arenes.

Authors: Xisheng Wang; Dasheng Leow; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2011-08-16 Impact factor: 15.419

2. Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

Authors: Tian-Sheng Mei; Lei Kou; Sandy Ma; Keary M Engle; Jin-Quan Yu
Journal: Synthesis (Stuttg) Date: 2012-05-25 Impact factor: 3.157

3. Formation of α-chiral centers by asymmetric β-C(sp3)-H arylation, alkenylation, and alkynylation.

Authors: Qing-Feng Wu; Peng-Xiang Shen; Jian He; Xiao-Bing Wang; Forrest Zhang; Qian Shao; Ru-Yi Zhu; Claudio Mapelli; Jennifer X Qiao; Michael A Poss; Jin-Quan Yu
Journal: Science Date: 2017-02-03 Impact factor: 47.728

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

Authors: Jian He; Masayuki Wasa; Kelvin S L Chan; Qian Shao; Jin-Quan Yu
Journal: Chem Rev Date: 2016-12-02 Impact factor: 60.622

5. 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

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

Authors: Gang Li; Dasheng Leow; Li Wan; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2012-12-13 Impact factor: 15.336

Review 7. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors: John C K Chu; Tomislav Rovis
Journal: Angew Chem Int Ed Engl Date: 2017-12-05 Impact factor: 15.336

Pd(II)-catalyzed olefination of sp3 C-H bonds.

1. Catalytic C-H bond functionalization with palladiumII: aerobic oxidative annulations of indoles.

2. The total synthesis of (+)-dragmacidin F.

3. Palladium-catalyzed intermolecular alkenylation of indoles by solvent-controlled regioselective C-H functionalization.

4. Directed palladation: fine tuning permits the catalytic 2-alkenylation of indoles.

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

6. Palladium-catalyzed cross-coupling reactions in total synthesis.

7. Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature.

8. Ligand-enabled reactivity and selectivity in a synthetically versatile aryl C-H olefination.

9. A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole --> dihydroindoloazocine cyclization.

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

1. Pd(II)-catalyzed para-selective C-H arylation of monosubstituted arenes.

2. Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

3. Formation of α-chiral centers by asymmetric β-C(sp3)-H arylation, alkenylation, and alkynylation.

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

5. 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.

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

Review 7. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

8. Highly Versatile β-C(sp³)-H Iodination of Ketones Using a Practical Auxiliary.

9. γ,δ,ε-C(sp(3))-H Functionalization through Directed Radical H-Abstraction.

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

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

Review 7. Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Review 7. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.