Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Stereospecific nickel-catalyzed cross-coupling reactions of alkyl Grignard reagents and identification of selective anti-breast-cancer agents.

Literature DB >> 24478275

Stereospecific nickel-catalyzed cross-coupling reactions of alkyl Grignard reagents and identification of selective anti-breast-cancer agents.

Ivelina M Yonova¹, A George Johnson¹, Charlotte A Osborne¹, Curtis E Moore², Naomi S Morrissette³, Elizabeth R Jarvo¹.

Abstract

Alkyl Grignard reagents that contain β-hydrogen atoms were used in a stereospecific nickel-catalyzed cross-coupling reaction to form C(sp(3))-C(sp(3)) bonds. Aryl Grignard reagents were also utilized to synthesize 1,1-diarylalkanes. Several compounds synthesized by this method exhibited selective inhibition of proliferation of MCF-7 breast cancer cells.

Entities: CellLine Chemical Disease Gene

Keywords: Kumada coupling; alkyl Grignard reagents; breast cancer; enantiospecificity; nickel

Mesh：

Substances：

Year: 2014 PMID： 24478275 PMCID： PMC3991427 DOI： 10.1002/anie.201308666

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

31 in total

1. Enantioselective preparation of 1,1-diarylethanes: aldehydes as removable steering groups for asymmetric synthesis.

Authors: Thomas C Fessard; Stephen P Andrews; Hajime Motoyoshi; Erick M Carreira
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

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. 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

4. Highly enantioselective hydrogenation of styrenes directed by 2'-hydroxyl groups.

Authors: Xiang Wang; Anil Guram; Seb Caille; Jack Hu; J P Preston; Michael Ronk; Shawn Walker
Journal: Org Lett Date: 2011-03-08 Impact factor: 6.005

5. Enantioconvergent cross-couplings of racemic alkylmetal reagents with unactivated secondary alkyl electrophiles: catalytic asymmetric Negishi α-alkylations of N-Boc-pyrrolidine.

Authors: Christopher J Cordier; Rylan J Lundgren; Gregory C Fu
Journal: J Am Chem Soc Date: 2013-07-19 Impact factor: 15.419

6. Density functional theory studies of negishi alkyl-alkyl cross-coupling reactions catalyzed by a methylterpyridyl-Ni(I) complex.

Authors: Xufeng Lin; David Lee Phillips
Journal: J Org Chem Date: 2008-04-15 Impact factor: 4.354

7. Acceleration of arylzinc formation and its enantioselective addition to aldehydes by microwave irradiation and aziridine-2-methanol catalysts.

Authors: Antonio L Braga; Marcio W Paixão; Bernhard Westermann; Paulo H Schneider; Ludger A Wessjohann
Journal: J Org Chem Date: 2008-03-04 Impact factor: 4.354

8. Functional-group-tolerant, nickel-catalyzed cross-coupling reaction for enantioselective construction of tertiary methyl-bearing stereocenters.

Authors: Hanna M Wisniewska; Elizabeth C Swift; Elizabeth R Jarvo
Journal: J Am Chem Soc Date: 2013-06-10 Impact factor: 15.419

9. Traceless directing group for stereospecific nickel-catalyzed alkyl-alkyl cross-coupling reactions.

Authors: Margaret A Greene; Ivelina M Yonova; Florence J Williams; Elizabeth R Jarvo
Journal: Org Lett Date: 2012-05-08 Impact factor: 6.005

10. Cross coupling reactions of chiral secondary organoboronic esters with retention of configuration.

Authors: Daisuke Imao; Ben W Glasspoole; Véronique S Laberge; Cathleen M Crudden
Journal: J Am Chem Soc Date: 2009-04-15 Impact factor: 15.419

24 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. 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

3. Enantiospecific sp(2)-sp(3) coupling of secondary and tertiary boronic esters.

Authors: Amadeu Bonet; Marcin Odachowski; Daniele Leonori; Stephanie Essafi; Varinder K Aggarwal
Journal: Nat Chem Date: 2014-06-08 Impact factor: 24.427

4. Keeping Track of the Electrons.

Authors: Erika L Lucas; Elizabeth R Jarvo
Journal: Acc Chem Res Date: 2018-01-24 Impact factor: 22.384

5. Well-defined nickel and palladium precatalysts for cross-coupling.

Authors: Nilay Hazari; Patrick R Melvin; Megan Mohadjer Beromi
Journal: Nat Rev Chem Date: 2017-03-01 Impact factor: 34.035

6. Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Authors: Louis-Charles Campeau; Nilay Hazari
Journal: Organometallics Date: 2018-11-27 Impact factor: 3.876

7. Mechanism and Origins of Ligand-Controlled Stereoselectivity of Ni-Catalyzed Suzuki-Miyaura Coupling with Benzylic Esters: A Computational Study.

Authors: Shuo-Qing Zhang; Buck L H Taylor; Chong-Lei Ji; Yuan Gao; Michael R Harris; Luke E Hanna; Elizabeth R Jarvo; K N Houk; Xin Hong
Journal: J Am Chem Soc Date: 2017-09-07 Impact factor: 15.419