Literature DB >> 24279380

Enantioselective, nickel-catalyzed Suzuki cross-coupling of quinolinium ions.

Jason D Shields1, Derek T Ahneman, Thomas J A Graham, Abigail G Doyle.   

Abstract

Quinolinium ions are engaged in an asymmetric, Ni-catalyzed Suzuki cross-coupling to yield 2-aryl- and 2-heteroaryl-1,2-dihydroquinolines. Key to the development of this method is the use of a Ni(II) precatalyst that activates without the need for strong reductants or high temperatures. The Ni-iminium activation mode is demonstrated as an exceptionally mild pathway to generate enantioenriched products from racemic starting materials.

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Year:  2013        PMID: 24279380      PMCID: PMC3924560          DOI: 10.1021/ol4031364

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  19 in total

1.  Enantioselective boronate additions to N-acyl quinoliniums catalyzed by tartaric acid.

Authors:  Tomohiro Kodama; Philip N Moquist; Scott E Schaus
Journal:  Org Lett       Date:  2011-11-08       Impact factor: 6.005

2.  A highly enantioselective Brønsted acid catalyzed cascade reaction: organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids.

Authors:  Magnus Rueping; Andrey P Antonchick; Thomas Theissmann
Journal:  Angew Chem Int Ed Engl       Date:  2006-05-26       Impact factor: 15.336

3.  Nickel(0) triethyl phosphite complex-catalyzed allylic substitution with retention of regio- and stereochemistry.

Authors:  Yasutaka Yatsumonji; Yusuke Ishida; Akira Tsubouchi; Takeshi Takeda
Journal:  Org Lett       Date:  2007-09-29       Impact factor: 6.005

4.  Catalytic enantioselective petasis-type reaction of quinolines catalyzed by a newly designed thiourea catalyst.

Authors:  Yousuke Yamaoka; Hideto Miyabe; Yoshiji Takemoto
Journal:  J Am Chem Soc       Date:  2007-05-08       Impact factor: 15.419

5.  Copper-catalyzed coupling of pyridines and quinolines with alkynes: a one-step, asymmetric route to functionalized heterocycles.

Authors:  Daniel A Black; Ramsay E Beveridge; Bruce A Arndtsen
Journal:  J Org Chem       Date:  2008-01-24       Impact factor: 4.354

6.  Nickel-catalyzed enantioselective cross-couplings of racemic secondary electrophiles that bear an oxygen leaving group.

Authors:  Alexander J Oelke; Jianwei Sun; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2012-02-01       Impact factor: 15.419

7.  Mechanistic investigation of the nickel-catalyzed Suzuki reaction of N,O-acetals: evidence for boronic acid assisted oxidative addition and an iminium activation pathway.

Authors:  Kevin T Sylvester; Kevin Wu; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2012-10-05       Impact factor: 15.419

8.  Simplifying nickel(0) catalysis: an air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes.

Authors:  Eric A Standley; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2013-01-14       Impact factor: 15.419

9.  Combined experimental and theoretical study on the reductive cleavage of inert C-O bonds with silanes: ruling out a classical Ni(0)/Ni(II) catalytic couple and evidence for Ni(I) intermediates.

Authors:  Josep Cornella; Enrique Gómez-Bengoa; Ruben Martin
Journal:  J Am Chem Soc       Date:  2013-01-23       Impact factor: 15.419

10.  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

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  15 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 Allylic Alkylation with Diarylmethane Pronucleophiles: Reaction Development and Mechanistic Insights.

Authors:  Sheng-Chun Sha; Hui Jiang; Jianyou Mao; Ana Bellomo; Soo A Jeong; Patrick J Walsh
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-03       Impact factor: 15.336

3.  Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates.

Authors:  Meredith S Eno; Alexander Lu; James P Morken
Journal:  J Am Chem Soc       Date:  2016-06-16       Impact factor: 15.419

4.  Parameterization of phosphine ligands demonstrates enhancement of nickel catalysis via remote steric effects.

Authors:  Kevin Wu; Abigail G Doyle
Journal:  Nat Chem       Date:  2017-03-06       Impact factor: 24.427

5.  Mechanistic Study of an Improved Ni Precatalyst for Suzuki-Miyaura Reactions of Aryl Sulfamates: Understanding the Role of Ni(I) Species.

Authors:  Megan Mohadjer Beromi; Ainara Nova; David Balcells; Ann M Brasacchio; Gary W Brudvig; Louise M Guard; Nilay Hazari; David J Vinyard
Journal:  J Am Chem Soc       Date:  2017-01-10       Impact factor: 15.419

6.  Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

Authors:  Zhiwei Zuo; Derek T Ahneman; Lingling Chu; Jack A Terrett; Abigail G Doyle; David W C MacMillan
Journal:  Science       Date:  2014-06-05       Impact factor: 47.728

7.  A modular, air-stable nickel precatalyst.

Authors:  Jason D Shields; Erin E Gray; Abigail G Doyle
Journal:  Org Lett       Date:  2015-04-17       Impact factor: 6.005

8.  Stereoconvergent arylations and alkenylations of unactivated alkyl electrophiles: catalytic enantioselective synthesis of secondary sulfonamides and sulfones.

Authors:  Junwon Choi; Pablo Martín-Gago; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2014-08-15       Impact factor: 15.419

9.  Nickel-catalyzed enantioselective arylation of pyridine.

Authors:  J Patrick Lutz; Stephen T Chau; Abigail G Doyle
Journal:  Chem Sci       Date:  2016-03-08       Impact factor: 9.825

10.  Catalytic enantioselective cyclization/cross-coupling with alkyl electrophiles.

Authors:  Huan Cong; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2014-02-27       Impact factor: 15.419

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