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Literature DB >> 25113669

Alkene carboboration enabled by synergistic catalysis.

Kevin B Smith¹, Kaitlyn M Logan, Wei You, M Kevin Brown.

Abstract

A synergistic Pd/Cu system for the coupling of alkenes, (Bpin)2 (pin = pinacolate), and aryl/vinyl bromides is disclosed. This method allows for the catalytic generation of secondary Csp(3)-Cu nucleophiles in situ and subsequent Pd-catalyzed cross-coupling.

Entities: Chemical

Keywords: carboboration; copper; cross-coupling; palladium; synergistic catalysis

Year: 2014 PMID： 25113669 DOI： 10.1002/chem.201404310

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

Keyword Cloud
Cited

30 in total

1. Catalytic Enantioselective Conjugate Additions of (pin)B-Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene.

Authors: Xiben Li; Fanke Meng; Sebastian Torker; Ying Shi; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2016-07-20 Impact factor: 15.336

2. A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal.

Authors: Xun Liu; T Maxwell Deaton; Fredrik Haeffner; James P Morken
Journal: Angew Chem Int Ed Engl Date: 2017-08-09 Impact factor: 15.336

3. 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 4. 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

10. Synthesis of Bisheteroarylalkanes by Heteroarylboration: Development and Application of a Pyridylidene-Copper Complex.

Authors: Yuan Huang; M Kevin Brown
Journal: Angew Chem Int Ed Engl Date: 2019-03-27 Impact factor: 15.336

Alkene carboboration enabled by synergistic catalysis.

1. Catalytic Enantioselective Conjugate Additions of (pin)B-Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene.

2. A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal.

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

Review 4. Palladium(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol by a Chiral Auxiliary.

5. Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

6. Copper-Catalyzed Borylacylation of Activated Alkenes with Acid Chlorides.

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

8. Catalytic Enantioselective Arylboration of Alkenylarenes.

9. A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.

10. Synthesis of Bisheteroarylalkanes by Heteroarylboration: Development and Application of a Pyridylidene-Copper Complex.