Literature DB >> 19943702

Palladium-catalyzed cross-coupling reaction of secondary benzylic bromides with grignard reagents.

Ana López-Pérez1, Javier Adrio, Juan C Carretero.   

Abstract

A mild palladium-catalyzed Kumada-Corriu reaction of secondary benzylic bromides with aryl and alkenyl Grignard reagents has been developed. In the presence of the Xantphos ligand, the undesired beta-elimination pathway is minimized, affording the corresponding cross-coupling products in acceptable to good yields. The reaction proceeds with inversion of the configuration.

Entities:  

Year:  2009        PMID： 19943702     DOI： 10.1021/ol902335c

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


  18 in total

1.  A General, Simple Catalyst for Enantiospecific Cross Couplings of Benzylic Ammonium Triflates and Boronic Acids: No Phosphine Ligand Required.

Authors:  Danielle M Shacklady-McAtee; Kelsey M Roberts; Corey H Basch; Ye-Geun Song; Mary P Watson
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

Review 2.  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

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.  Retention or inversion in stereospecific nickel-catalyzed cross-coupling of benzylic carbamates with arylboronic esters: control of absolute stereochemistry with an achiral catalyst.

Authors:  Michael R Harris; Luke E Hanna; Margaret A Greene; Curtis E Moore; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2013-02-22       Impact factor: 15.419

5.  Asymmetric transition metal-catalyzed cross-coupling reactions for the construction of tertiary stereocenters.

Authors:  Elizabeth C Swift; Elizabeth R Jarvo
Journal:  Tetrahedron       Date:  2013-07-22       Impact factor: 2.457

6.  Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: stereospecific formation of diarylalkanes and triarylmethanes.

Authors:  Qi Zhou; Harathi D Srinivas; Srimoyee Dasgupta; Mary P Watson
Journal:  J Am Chem Soc       Date:  2013-02-20       Impact factor: 15.419

7.  Asymmetric synthesis via stereospecific C-N and C-O bond activation of alkyl amine and alcohol derivatives.

Authors:  Sarah M Pound; Mary P Watson
Journal:  Chem Commun (Camb)       Date:  2018-10-30       Impact factor: 6.222

8.  Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles.

Authors:  Benjamin J Stokes; Susanne M Opra; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2012-07-06       Impact factor: 15.419

9.  Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1'-diarylbutyl pharmacophore.

Authors:  Nivedita S Mahajani; John D Chisholm
Journal:  Org Biomol Chem       Date:  2018-05-30       Impact factor: 3.876

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

Authors:  Ivelina M Yonova; A George Johnson; Charlotte A Osborne; Curtis E Moore; Naomi S Morrissette; Elizabeth R Jarvo
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-29       Impact factor: 15.336
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