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Literature DB >> 28000415

Catalytic Enantioselective Arylboration of Alkenylarenes.

Abstract

A method for the catalytic enantioselective arylboration of alkenylarenes is disclosed. The reaction leads to the formation of 1,1-diarylalkanes that also incorporate an additional pinacol boronic ester which can be easily transformed to a variety of groups. The products are formed with excellent diastereoselectivities and enantioselectivities.

Entities: Chemical Disease Gene

Keywords: alkenes; copper; cross-coupling; enantioselective catalysis; palladium

Mesh：

Substances：

Year: 2016 PMID： 28000415 PMCID： PMC5225072 DOI： 10.1002/anie.201609844

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

40 in total

Review 1. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors: Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal: Chem Rev Date: 2015-08-13 Impact factor: 60.622

2. Copper/palladium synergistic catalysis for the syn- and anti-selective carboboration of alkenes.

Authors: Kaitlyn M Logan; Kevin B Smith; M Kevin Brown
Journal: Angew Chem Int Ed Engl Date: 2015-02-27 Impact factor: 15.336

Review 3. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors: Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal: Chem Rev Date: 2011-02-14 Impact factor: 60.622

4. Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes.

Authors: Brooks E Maki; Audrey Chan; Eric M Phillips; Karl A Scheidt
Journal: Org Lett Date: 2007-01-18 Impact factor: 6.005

5. Enantioselective, palladium-catalyzed alpha-arylation of N-Boc-pyrrolidine.

Authors: Kevin R Campos; Artis Klapars; Jacob H Waldman; Peter G Dormer; Cheng-yi Chen
Journal: J Am Chem Soc Date: 2006-03-22 Impact factor: 15.419

6. Distinctive meta-directing group effect for iridium-catalyzed 1,1-diarylalkene enantioselective hydrogenation.

Authors: Elizabeth N Bess; Matthew S Sigman
Journal: Org Lett Date: 2013-01-11 Impact factor: 6.005

7. Enantioselective synthesis of alpha,alpha-disubstituted cyclopentenes by an N-heterocyclic carbene-catalyzed desymmetrization of 1,3-diketones.

Authors: Manabu Wadamoto; Eric M Phillips; Troy E Reynolds; Karl A Scheidt
Journal: J Am Chem Soc Date: 2007-07-31 Impact factor: 15.419

8. Nickel/bis(oxazoline)-catalyzed asymmetric Negishi arylations of racemic secondary benzylic electrophiles to generate enantioenriched 1,1-diarylalkanes.

Authors: Hien-Quang Do; E R R Chandrashekar; Gregory C Fu
Journal: J Am Chem Soc Date: 2013-10-28 Impact factor: 15.419

9. Stereospecific pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides.

Authors: Ling Li; Shibin Zhao; Amruta Joshi-Pangu; Mohamed Diane; Mark R Biscoe
Journal: J Am Chem Soc Date: 2014-09-23 Impact factor: 15.419

10. Diastereo- and enantioselective reactions of bis(pinacolato)diboron, 1,3-enynes, and aldehydes catalyzed by an easily accessible bisphosphine-Cu complex.

Authors: Fanke Meng; Fredrik Haeffner; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2014-08-04 Impact factor: 15.419

29 in total

1. Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes.

Authors: Kelsey E Poremba; Nathaniel T Kadunce; Naoyuki Suzuki; Alan H Cherney; Sarah E Reisman
Journal: J Am Chem Soc Date: 2017-04-13 Impact factor: 15.419

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

3. Differential Dihydrofunctionalization of Terminal Alkynes: Synthesis of Benzylic Alkyl Boronates through Reductive Three-Component Coupling.

Authors: Megan K Armstrong; Gojko Lalic
Journal: J Am Chem Soc Date: 2019-04-03 Impact factor: 15.419

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

Authors: Yuan Huang; Kevin B Smith; M Kevin Brown
Journal: Angew Chem Int Ed Engl Date: 2017-09-18 Impact factor: 15.336

6. Mechanism-based enhancement of scope and enantioselectivity for reactions involving a copper-substituted stereogenic carbon centre.

Authors: Jaehee Lee; Suttipol Radomkit; Sebastian Torker; Juan Del Pozo; Amir H Hoveyda
Journal: Nat Chem Date: 2017-10-02 Impact factor: 24.427

7. 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

8. Stereospecific Synthesis of E-Alkenes through Anti-Markovnikov Hydroalkylation of Terminal Alkynes.

Authors: Avijit Hazra; Jason Chen; Gojko Lalic
Journal: J Am Chem Soc Date: 2019-08-02 Impact factor: 15.419

9. 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

10. Organoboron chemistry comes to light: recent advances in photoinduced synthetic approaches to organoboron compounds.

Authors: Viet D Nguyen; Vu T Nguyen; Shengfei Jin; Hang T Dang; Oleg V Larionov
Journal: Tetrahedron Date: 2018-12-24 Impact factor: 2.457