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Literature DB >> 22356620

Intramolecular Pd(II)-catalyzed aerobic oxidative amination of alkenes: synthesis of six-membered N-heterocycles.

Abstract

Use of a base-free Pd(DMSO)(2)(TFA)(2) catalyst system enables the synthesis of six-membered nitrogen heterocycles via a Wacker-type aerobic oxidative cyclization of alkenes bearing tethered sulfonamides. Various heterocycles, including morpholines, piperidines, piperazines, and piperazinones, are accessible by this method.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2012 PMID： 22356620 PMCID： PMC3298079 DOI： 10.1021/ol300030w

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

42 in total

1. Palladium(II)-Catalyzed Cyclization of Olefinic Tosylamides.

Authors: Richard C. Larock; Timothy R. Hightower; Lisa A. Hasvold; Karl P. Peterson
Journal: J Org Chem Date: 1996-05-31 Impact factor: 4.354

2. Gold(I)-catalyzed intramolecular hydroamination of alkenyl carbamates.

Authors: Xiaoqing Han; Ross A Widenhoefer
Journal: Angew Chem Int Ed Engl Date: 2006-03-03 Impact factor: 15.336

Review 3. Hydroamination: direct addition of amines to alkenes and alkynes.

Authors: Thomas E Müller; Kai C Hultzsch; Miguel Yus; Francisco Foubelo; Mizuki Tada
Journal: Chem Rev Date: 2008-08-26 Impact factor: 60.622

4. Intramolecular hydroamination of unbiased and functionalized primary aminoalkenes catalyzed by a rhodium aminophosphine complex.

Authors: Lisa D Julian; John F Hartwig
Journal: J Am Chem Soc Date: 2010-10-06 Impact factor: 15.419

5. Intramolecular anodic olefin coupling reactions and the synthesis of cyclic amines.

Authors: Hai-Chao Xu; Kevin D Moeller
Journal: J Am Chem Soc Date: 2010-03-03 Impact factor: 15.419

6. Synthesis of heterocycles via palladium pi-olefin and pi-alkyne chemistry.

Authors: Gilson Zeni; Richard C Larock
Journal: Chem Rev Date: 2004-05 Impact factor: 60.622

7. 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

8. Ligand-modulated palladium-catalyzed aerobic alcohol oxidations.

Authors: Matthew S Sigman; David R Jensen
Journal: Acc Chem Res Date: 2006-03 Impact factor: 22.384

Review 9. Palladium oxidase catalysis: selective oxidation of organic chemicals by direct dioxygen-coupled turnover.

Authors: Shannon S Stahl
Journal: Angew Chem Int Ed Engl Date: 2004-06-28 Impact factor: 15.336

10. Palladium-catalyzed aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions.

Authors: Vasily Kotov; Christopher C Scarborough; Shannon S Stahl
Journal: Inorg Chem Date: 2007-03-19 Impact factor: 5.165

12 in total

1. Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes.

Authors: Fatima C Sequeira; Sherry R Chemler
Journal: Org Lett Date: 2012-08-15 Impact factor: 6.005

2. Diazafluorenone-Promoted Oxidation Catalysis: Insights into the Role of Bidentate Ligands in Pd-Catalyzed Aerobic Aza-Wacker Reactions.

Authors: Paul B White; Jonathan N Jaworski; Geyunjian Harry Zhu; Shannon S Stahl
Journal: ACS Catal Date: 2016-03-11 Impact factor: 13.084

3. A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of 4-Chloropiperidines from Homoallylic Amines.

Authors: Rene Ebule; Sagar Mudshinge; Michael H Nantz; Mark S Mashuta; Gerald B Hammond; Bo Xu
Journal: J Org Chem Date: 2019-02-27 Impact factor: 4.354

4. Synthesis of Indolines and Derivatives by Aza-Heck Cyclization.

Authors: Feiyang Xu; Katerina M Korch; Donald A Watson
Journal: Angew Chem Int Ed Engl Date: 2019-08-13 Impact factor: 15.336

5. Lewis Acid-Catalyzed Halonium Generation for Morpholine Synthesis and Claisen Rearrangement.

Authors: Jeewani P Ariyarathna; Nur-E Alom; Leo P Roberts; Navdeep Kaur; Fan Wu; Wei Li
Journal: J Org Chem Date: 2022-02-10 Impact factor: 4.198

6. Characterization of DMSO coordination to palladium(II) in solution and insights into the aerobic oxidation catalyst, Pd(DMSO)2(TFA)2.

Authors: Tianning Diao; Paul White; Ilia Guzei; Shannon S Stahl
Journal: Inorg Chem Date: 2012-10-23 Impact factor: 5.165

7. Mechanistic studies of Wacker-type amidocyclization of alkenes catalyzed by (IMes)Pd(TFA)2(H2O): kinetic and stereochemical implications of proton transfer.

Authors: Xuan Ye; Paul B White; Shannon S Stahl
Journal: J Org Chem Date: 2012-11-30 Impact factor: 4.354