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Literature DB >> 33395309

Mechanism-Based Design of an Amide-Directed Ni-Catalyzed Arylboration of Cyclopentene Derivatives.

Alison L Lambright¹, Yanyao Liu¹, Isaac A Joyner¹, Kaitlyn M Logan¹, M Kevin Brown¹.

Abstract

A method for amide-directed Ni-catalyzed diastereoselective arylboration of cyclopentenes is disclosed. The reaction allows for the synthesis of sterically congested cyclopentane scaffolds that contain an easily derivatized boronic ester and amide functional handles. The nature of the amide directing group and its influence on the reaction outcome are investigated and ultimately reflect a predictably selective reaction based on the solvent and base counterion.

Entities: Chemical

Mesh：

Substances：

Year: 2021 PMID： 33395309 PMCID： PMC7824974 DOI： 10.1021/acs.orglett.0c04208

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

33 in total

1. Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling.

Authors: Joseph Derosa; Van T Tran; Mark N Boulous; Jason S Chen; Keary M Engle
Journal: J Am Chem Soc Date: 2017-07-28 Impact factor: 15.419

2. Ni-Catalyzed Arylboration of Unactivated Alkenes: Scope and Mechanistic Studies.

Authors: Stephen R Sardini; Alison L Lambright; Grace L Trammel; Humair M Omer; Peng Liu; M Kevin Brown
Journal: J Am Chem Soc Date: 2019-06-04 Impact factor: 15.419

3. Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides.

Authors: Joseph Derosa; Roman Kleinmans; Van T Tran; Malkanthi K Karunananda; Steven R Wisniewski; Martin D Eastgate; Keary M Engle
Journal: J Am Chem Soc Date: 2018-12-17 Impact factor: 15.419

4. Regioselective Arylboration of Isoprene and Its Derivatives by Pd/Cu Cooperative Catalysis.

Authors: Kevin B Smith; M Kevin Brown
Journal: J Am Chem Soc Date: 2017-06-05 Impact factor: 15.419

5. Pd-Catalyzed Regioselective Arylboration of Vinylarenes.

Authors: Kai Yang; Qiuling Song
Journal: Org Lett Date: 2016-10-27 Impact factor: 6.005

6. Nickel-Catalyzed Arylboration of Alkenylarenes: Synthesis of Boron-Substituted Quaternary Carbons and Regiodivergent Reactions.

Authors: Liang-An Chen; Alan R Lear; Pin Gao; M Kevin Brown
Journal: Angew Chem Int Ed Engl Date: 2019-06-28 Impact factor: 15.336

7. Stereospecific functionalizations and transformations of secondary and tertiary boronic esters.

Authors: Christopher Sandford; Varinder K Aggarwal
Journal: Chem Commun (Camb) Date: 2017-05-17 Impact factor: 6.222

8. Directed, Palladium(II)-Catalyzed Enantioselective anti-Carboboration of Alkenyl Carbonyl Compounds.

Authors: Zhen Liu; Xiaohan Li; Tian Zeng; Keary M Engle
Journal: ACS Catal Date: 2019-03-13 Impact factor: 13.084

9. Copper-Catalyzed Heteroarylboration of 1,3-Dienes with 3-Bromopyridines: A cine Substitution.

Authors: Kevin B Smith; Yuan Huang; M Kevin Brown
Journal: Angew Chem Int Ed Engl Date: 2018-04-26 Impact factor: 15.336

10. Nickel-catalyzed difunctionalization of allyl moieties using organoboronic acids and halides with divergent regioselectivities.

Authors: Wanfang Li; Jie Kang Boon; Yu Zhao
Journal: Chem Sci Date: 2017-10-26 Impact factor: 9.825

3 in total