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Literature DB >> 22765909

Palladium-catalyzed 1,1-difunctionalization of ethylene.

Abstract

The 1,1-difunctionalization of ethylene, with aryl/vinyl/heteroaryl transmetalating agents and vinyl electrophiles, is reported. The reaction is high-yielding under a low pressure of ethylene, and regioselectivity is generally high for the 1,1-disubstituted product. The process is highlighted by the use of heteroaromatic cross-coupling reagents, which have not been competent reaction partners in previously reported efforts.

Entities: Chemical Disease Gene

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Year: 2012 PMID： 22765909 PMCID： PMC3459322 DOI： 10.1021/ja304344h

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

34 in total

1. Asymmetric hydrovinylation reaction.

Authors: T V RajanBabu
Journal: Chem Rev Date: 2003-08 Impact factor: 60.622

2. Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction.

Authors: Tejas P Pathak; Keith M Gligorich; Bryan E Welm; Matthew S Sigman
Journal: J Am Chem Soc Date: 2010-06-16 Impact factor: 15.419

3. A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids.

Authors: Longyan Liao; Ranjan Jana; Kaveri Balan Urkalan; Matthew S Sigman
Journal: J Am Chem Soc Date: 2011-03-30 Impact factor: 15.419

4. Ethylene in organic synthesis. Repetitive hydrovinylation of alkenes for highly enantioselective syntheses of pseudopterosins.

Authors: Daniel J Mans; G Adam Cox; T V RajanBabu
Journal: J Am Chem Soc Date: 2011-03-30 Impact factor: 15.419

5. Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors: Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2005-04-06 Impact factor: 15.419

6. Ethylene-promoted versus ethylene-free enyne metathesis.

Authors: Anne G D Grotevendt; Justin A M Lummiss; Melanie L Mastronardi; Deryn E Fogg
Journal: J Am Chem Soc Date: 2011-09-15 Impact factor: 15.419

7. Terminal Alkyne-Ethylene Cross-Metathesis: Reaction of 1-Substituted Propargyl Esters at Elevated Ethylene Pressure.

Authors:
Journal: J Org Chem Date: 2000-03-24 Impact factor: 4.354

8. Palladium-catalyzed cross-coupling reactions of pyridylboronic acids with heteroaryl halides bearing a primary amine group: synthesis of highly substituted bipyridines and pyrazinopyridines.

Authors: Amy E Thompson; Gregory Hughes; Andrei S Batsanov; Martin R Bryce; Paul R Parry; Brian Tarbit
Journal: J Org Chem Date: 2005-01-07 Impact factor: 4.354

Review 9. pi-Acidic alkene ligand effects in Pd-catalysed cross-coupling processes: exploiting the interaction of dibenzylidene acetone (dba) and related ligands with Pd(0) and Pd(II).

Authors: Ian J S Fairlamb
Journal: Org Biomol Chem Date: 2008-09-09 Impact factor: 3.876

10. A general solution for the 2-pyridyl problem.

Authors: Graham R Dick; Eric M Woerly; Martin D Burke
Journal: Angew Chem Int Ed Engl Date: 2012-01-27 Impact factor: 15.336

20 in total

1. Enantioselective 1,1-arylborylation of alkenes: merging chiral anion phase transfer with Pd catalysis.

Authors: Hosea M Nelson; Brett D Williams; Javier Miró; F Dean Toste
Journal: J Am Chem Soc Date: 2015-02-27 Impact factor: 15.419

2. Mechanistic Investigations of the Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Benzyl Acrylates.

Authors: Manuel Orlandi; Margaret J Hilton; Eiji Yamamoto; F Dean Toste; Matthew S Sigman
Journal: J Am Chem Soc Date: 2017-08-30 Impact factor: 15.419

3. Palladium-Catalyzed 1,3-Difunctionalization Using Terminal Alkenes with Alkenyl Nonaflates and Aryl Boronic Acids.

Authors: Matthew S McCammant; Takashi Shigeta; Matthew S Sigman
Journal: Org Lett Date: 2016-03-28 Impact factor: 6.005

4. Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives.

Authors: Shekhar Kc; Roshan K Dhungana; Namrata Khanal; Ramesh Giri
Journal: Angew Chem Int Ed Engl Date: 2020-03-19 Impact factor: 15.336

5. Catalyst-Controlled 1,2- and 1,1-Arylboration of α-Alkyl Alkenyl Arenes.

Authors: Allison M Bergmann; Stanna K Dorn; Kevin B Smith; Kaitlyn M Logan; M Kevin Brown
Journal: Angew Chem Int Ed Engl Date: 2019-01-09 Impact factor: 15.336

6. Palladium-catalyzed enantioselective Heck alkenylation of acyclic alkenols using a redox-relay strategy.

Authors: Harshkumar H Patel; Matthew S Sigman
Journal: J Am Chem Soc Date: 2015-03-09 Impact factor: 15.419

7. Pd(0)-catalyzed 1,1-diarylation of ethylene and allylic carbonates.

Authors: Vaneet Saini; Longyan Liao; Qiaofeng Wang; Ranjan Jana; Matthew S Sigman
Journal: Org Lett Date: 2013-09-18 Impact factor: 6.005

8. Development and Analysis of a Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Acrylates Enabled by Chiral Anion Phase Transfer.

Authors: Eiji Yamamoto; Margaret J Hilton; Manuel Orlandi; Vaneet Saini; F Dean Toste; Matthew S Sigman
Journal: J Am Chem Soc Date: 2016-11-30 Impact factor: 15.419

9. Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

Authors: Matthew S McCammant; Longyan Liao; Matthew S Sigman
Journal: J Am Chem Soc Date: 2013-03-12 Impact factor: 15.419

Review 10. Transition-metal-catalyzed laboratory-scale carbon-carbon bond-forming reactions of ethylene.

Authors: Vaneet Saini; Benjamin J Stokes; Matthew S Sigman
Journal: Angew Chem Int Ed Engl Date: 2013-09-17 Impact factor: 15.336