Literature DB >> 29271650

Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

Kaitlyn M Logan1, Stephen R Sardini1, Sean D White1, M Kevin Brown1.   

Abstract

A Ni-catalyzed method for arylboration is disclosed. The method allows for highly stereoselective arylboration of unactivated alkenes. The reactions utilize a simple Ni-catalyst and work with a broad range of alkenes and aryl bromides. The products represent useful intermediates for chemical synthesis due to the versatility of the C-B bond. Preliminary mechanistic details of the method are also disclosed.

Entities:  

Mesh：

Substances：

Year:  2017        PMID： 29271650      PMCID： PMC5778876          DOI： 10.1021/jacs.7b12160

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


  46 in total

1.  Nickel-catalyzed borylative ring-opening reaction of vinylcyclopropanes with bis(pinacolato)diboron yielding allylic boronates.

Authors:  Yuto Sumida; Hideki Yorimitsu; Koichiro Oshima
Journal:  Org Lett       Date:  2008-09-23       Impact factor: 6.005

Review 2.  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

3.  Stereospecific synthesis of cyclobutylboronates through copper(I)-catalyzed reaction of homoallylic sulfonates and a diboron derivative.

Authors:  Hajime Ito; Takashi Toyoda; Masaya Sawamura
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

4.  Enantioselective synthesis of trans-aryl- and -heteroaryl-substituted cyclopropylboronates by copper(I)-catalyzed reactions of allylic phosphates with a diboron derivative.

Authors:  Chongmin Zhong; Shun Kunii; Yuki Kosaka; Masaya Sawamura; Hajime Ito
Journal:  J Am Chem Soc       Date:  2010-08-25       Impact factor: 15.419

5.  Nickel-catalyzed trans-alkynylboration of alkynes via activation of a boron-chlorine bond.

Authors:  Akihiko Yamamoto; Michinori Suginome
Journal:  J Am Chem Soc       Date:  2005-11-16       Impact factor: 15.419

6.  Diastereoselective construction of functionalized homoallylic alcohols by Ni-catalyzed diboron-promoted coupling of dienes and aldehydes.

Authors:  Hee Yeon Cho; James P Morken
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

7.  Nickel-catalyzed borylative ring opening of vinyl epoxides and aziridines.

Authors:  Stefano Crotti; Ferruccio Bertolini; Franco Macchia; Mauro Pineschi
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

8.  Nickel-catalyzed beta-boration of alpha,beta-unsaturated esters and amides with bis(pinacolato)diboron.

Authors:  Koji Hirano; Hideki Yorimitsu; Koichiro Oshima
Journal:  Org Lett       Date:  2007-11-01       Impact factor: 6.005

9.  Diastereoselective reduction of alkenylboronic esters as a new method for controlling the stereochemistry of up to three adjacent centers in cyclic and acyclic molecules.

Authors:  Eike Hupe; Ilan Marek; Paul Knochel
Journal:  Org Lett       Date:  2002-08-22       Impact factor: 6.005

10.  Synthesis of optically active boron-silicon bifunctional cyclopropane derivatives through enantioselective copper(I)-catalyzed reaction of allylic carbonates with a diboron derivative.

Authors:  Hajime Ito; Yuki Kosaka; Kousuke Nonoyama; Yusuke Sasaki; Masaya Sawamura
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336
View more
  24 in total

1.  Nickel-Catalyzed Arylboration of Cyclopentene.

Authors:  Stephen R Sardini; M Kevin Brown
Journal:  Organic Synth       Date:  2020

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

Review 3.  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

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

Authors:  Stephen R Sardini; Alison L Lambright; Grace L Trammel; Humair M Omer; Peng Liu; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2019-06-04       Impact factor: 15.419

5.  Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones.

Authors:  Joseph M Zanghi; Shuang Liu; Simon J Meek
Journal:  Org Lett       Date:  2019-06-14       Impact factor: 6.005

6.  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

7.  Nickel-Catalyzed Stereoselective Diarylation of Alkenylarenes.

Authors:  Pin Gao; Liang-An Chen; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2018-08-20       Impact factor: 15.419

8.  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

9.  Catalytic Carbo- and Aminoboration of Alkenyl Carbonyl Compounds via Five- and Six-Membered Palladacycles.

Authors:  Zhen Liu; Hui-Qi Ni; Tian Zeng; Keary M Engle
Journal:  J Am Chem Soc       Date:  2018-02-07       Impact factor: 15.419

10.  Directed, Palladium(II)-Catalyzed Enantioselective anti-Carboboration of Alkenyl Carbonyl Compounds.

Authors:  Zhen Liu; Xiaohan Li; Tian Zeng; Keary M Engle
Journal:  ACS Catal       Date:  2019-03-13       Impact factor: 13.084
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.