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Literature DB >> 23837686

Ligand-controlled palladium-catalyzed regiodivergent Suzuki-Miyaura cross-coupling of allylboronates and aryl halides.

Abstract

An orthogonal set of catalyst systems has been developed for the Suzuki-Miyaura coupling of 3,3-disubstituted and 3-monosubstituted allylboronates with (hetero)aryl halides. These methods allow for the highly selective preparation of either the α- or the γ-isomeric coupling product.

Entities: Chemical Disease Gene

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Year: 2013 PMID： 23837686 PMCID： PMC3776608 DOI： 10.1021/ja405950c

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

17 in total

Review 1. Prenylated indole derivatives from fungi: structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis.

Authors: Shu-Ming Li
Journal: Nat Prod Rep Date: 2009-11-19 Impact factor: 13.423

2. Ni- and Pd-catalyzed synthesis of substituted and functionalized allylic boronates.

Authors: Ping Zhang; Ian A Roundtree; James P Morken
Journal: Org Lett Date: 2012-02-29 Impact factor: 6.005

3. 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

Review 4. Indole prenylation in alkaloid synthesis.

Authors: Thomas Lindel; Nils Marsch; Santosh Kumar Adla
Journal: Top Curr Chem Date: 2012

5. Palladium-catalyzed coupling of allylboronic acids with iodobenzenes. Selective formation of the branched allylic product in the absence of directing groups.

Authors: Sara Sebelius; Vilhelm J Olsson; Olov A Wallner; Kalman J Szabó
Journal: J Am Chem Soc Date: 2006-06-28 Impact factor: 15.419

6. A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

Authors: Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2010-10-13 Impact factor: 15.419

7. Suzuki-Miyaura cross-couplings of secondary allylic boronic esters.

Authors: Ben W Glasspoole; Kazem Ghozati; Jonathon W Moir; Cathleen M Crudden
Journal: Chem Commun (Camb) Date: 2011-12-19 Impact factor: 6.222

8. Highly regio- and stereoselective synthesis of (Z)-trisubstituted alkenes via propyne bromoboration and tandem Pd-catalyzed cross-coupling.

Authors: Chao Wang; Tomas Tobrman; Zhaoqing Xu; Ei-ichi Negishi
Journal: Org Lett Date: 2009-09-17 Impact factor: 6.005

9. Efficient and stereoselective synthesis of yellow scale pheromone via alkyne haloboration, Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction), and Pd-catalyzed tandem Negishi coupling.

Authors: Zhaoqing Xu; Ei-Ichi Negishi
Journal: Org Lett Date: 2008-09-03 Impact factor: 6.005

10. Palladium-catalyzed synthesis and isolation of functionalized allylboronic acids: selective, direct allylboration of ketones.

Authors: Mihai Raducan; Rauful Alam; Kálmán J Szabó
Journal: Angew Chem Int Ed Engl Date: 2012-11-19 Impact factor: 15.336

25 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. Modular, Catalytic Enantioselective Construction of Quaternary Carbon Stereocenters by Sequential Cross-Coupling Reactions.

Authors: Bowman Potter; Emma K Edelstein; James P Morken
Journal: Org Lett Date: 2016-06-16 Impact factor: 6.005

3. NHC Ligands Tailored for Simultaneous Regio- and Enantiocontrol in Nickel-Catalyzed Reductive Couplings.

Authors: Hengbin Wang; Gang Lu; Grant J Sormunen; Hasnain A Malik; Peng Liu; John Montgomery
Journal: J Am Chem Soc Date: 2017-07-03 Impact factor: 15.419

4. Palladium-catalyzed completely linear-selective Negishi cross-coupling of allylzinc halides with aryl and vinyl electrophiles.

Authors: Yang Yang; Thomas J L Mustard; Paul Ha-Yeon Cheong; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2013-11-08 Impact factor: 15.336

5. Cu-Catalyzed Diastereo- and Enantioselective Reactions of γ,γ-Disubstituted Allyldiboron Compounds with Ketones.

Authors: Joseph M Zanghi; Simon J Meek
Journal: Angew Chem Int Ed Engl Date: 2020-03-24 Impact factor: 15.336

6. Catalyst Controlled Regiodivergent Arylboration of Dienes.

Authors: Stephen R Sardini; M Kevin Brown
Journal: J Am Chem Soc Date: 2017-07-12 Impact factor: 15.419

7. 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

8. Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents.

Authors: Emma K Edelstein; Sheila Namirembe; James P Morken
Journal: J Am Chem Soc Date: 2017-03-29 Impact factor: 15.419

9. Enantioselective total synthesis of (-)-lansai B and (+)-nocardioazines A and B.

Authors: Haoxuan Wang; Sarah E Reisman
Journal: Angew Chem Int Ed Engl Date: 2014-04-28 Impact factor: 15.336

10. Diastereo-, Enantio-, and anti-Selective Formation of Secondary Alcohol and Quaternary Carbon Stereocenters by Cu-Catalyzed Additions of B-Substituted Allyl Nucleophiles to Carbonyls.

Authors: Emilie Wheatley; Joseph M Zanghi; Simon J Meek
Journal: Org Lett Date: 2020-11-18 Impact factor: 6.005