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Literature DB >> 29095636

Copper-Catalyzed Asymmetric Borylallylation of Vinyl Arenes.

Namhyeon Kim¹, Jung Tae Han¹, Do Hyun Ryu¹, Jaesook Yun¹.

Abstract

A copper-catalyzed, enantioselective method for the borylallylation of vinyl arenes is reported. The reaction produces enantioenriched and functionalized organoboron compounds by sequentially incorporating boryl and allyl groups onto the C═C bond of vinyl arenes. Copper-catalyzed borylative coupling of vinyl arenes with allyl phosphates successfully proceeds in a regio- and enantioselective manner in the absence of a palladium cocatalyst.

Entities: Chemical

Year: 2017 PMID： 29095636 DOI： 10.1021/acs.orglett.7b03022

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

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Cited

8 in total

1. 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 2. 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

3. Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates.

Authors: Youming Huang; Juan Del Pozo; Sebastian Torker; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2018-02-08 Impact factor: 15.419

4. Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid.

Authors: Erin N Hancock; Erin L Kuker; Dean J Tantillo; M Kevin Brown
Journal: Angew Chem Int Ed Engl Date: 2019-11-18 Impact factor: 15.336

Review 5. Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates.

Authors: Weichao Xue; Martin Oestreich
Journal: ACS Cent Sci Date: 2020-07-09 Impact factor: 14.553

Copper-Catalyzed Asymmetric Borylallylation of Vinyl Arenes.

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

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

3. Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates.

4. Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid.

Review 5. Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates.

6. Diastereo- and enantioselective copper catalyzed hydroallylation of disubstituted cyclopropenes.

7. Enantio- and Diastereoselective Copper-Catalyzed Allylboration of Alkynes with Allylic gem-Dichlorides.

8. Transition Metal-Free 1,2-Carboboration of Unactivated Alkenes.