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Literature DB >> 26338141

Ligand-Controlled Regiodivergent Copper-Catalyzed Alkylboration of Alkenes.

Wei Su¹, Tian-Jun Gong¹, Xi Lu¹, Meng-Yu Xu¹, Chu-Guo Yu¹, Zheng-Yang Xu¹, Hai-Zhu Yu¹, Bin Xiao², Yao Fu³.

Abstract

A novel copper-catalyzed regiodivergent alkylboration of alkenes with bis(pinacolato)diboron and alkyl halides has been developed. The regioselectivity of the alkylboration was controlled by subtle differences in the ligand structure. The reaction thus enables the practical, regiodivergent synthesis of two different alkyl boronic esters with complex structures from a single alkene.

Entities: Chemical

Keywords: copper; cross-coupling; difunctionalization; homogeneous catalysis; synthetic methods

Mesh：

Substances：

Year: 2015 PMID： 26338141 DOI： 10.1002/anie.201506713

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

23 in total

1. Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement.

Authors: Liang Zhang; Gabriel J Lovinger; Emma K Edelstein; Adam A Szymaniak; Matteo P Chierchia; James P Morken
Journal: Science Date: 2016-01-01 Impact factor: 47.728

2. Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

Authors: Zhen Liu; Yang Gao; Tian Zeng; Keary M Engle
Journal: Isr J Chem Date: 2019-09-10 Impact factor: 3.333

Review 3. Palladium(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol by a Chiral Auxiliary.

Authors: Zhen Liu; Jiahao Chen; Hou-Xiang Lu; Xiaohan Li; Yang Gao; John R Coombs; Matthew J Goldfogel; Keary M Engle
Journal: Angew Chem Int Ed Engl Date: 2019-10-08 Impact factor: 15.336

4. Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

Authors: Kaitlyn M Logan; Stephen R Sardini; Sean D White; M Kevin Brown
Journal: J Am Chem Soc Date: 2017-12-22 Impact factor: 15.419

5. 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

6. Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones.

Authors: Joseph M Zanghi; Shuang Liu; Simon J Meek
Journal: Org Lett Date: 2019-06-14 Impact factor: 6.005

Ligand-Controlled Regiodivergent Copper-Catalyzed Alkylboration of Alkenes.

1. Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement.

2. Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

Review 3. Palladium(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol by a Chiral Auxiliary.

4. Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

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

6. Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones.

7. Synthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes.

8. Ligand-Controlled Regiodivergent Enantioselective Rhodium-Catalyzed Alkene Hydroboration.

9. Catalytic Carbo- and Aminoboration of Alkenyl Carbonyl Compounds via Five- and Six-Membered Palladacycles.

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