Literature DB >> 22746254

Palladium-catalyzed, asymmetric Mizoroki-Heck reaction of benzylic electrophiles using phosphoramidites as chiral ligands.

Zhigang Yang1, Jianrong Zhou.   

Abstract

We report herein the first examples of asymmetric Mizoroki-Heck reactions using benzyl electrophiles. A new phosphoramidite was identified to be an effective chiral ligand in the palladium-catalyzed reaction. The reaction is compatible with polar functional groups and can be readily scaled up. Several cyclic olefins worked well as olefin components. Thirty-one examples are included.

Entities:  

Year:  2012        PMID: 22746254     DOI: 10.1021/ja304099j

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


  9 in total

1.  Allylic functionalization of unactivated olefins with Grignard reagents.

Authors:  Hongli Bao; Liela Bayeh; Uttam K Tambar
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-23       Impact factor: 15.336

2.  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

3.  Preparation and Applications of 4-Methoxybenzyl Esters in Organic Synthesis.

Authors:  Kyle T Howard; John D Chisholm
Journal:  Org Prep Proced Int       Date:  2016-01-29       Impact factor: 1.628

4.  Transition-Metal-Catalyzed Alkyl Heck-Type Reactions.

Authors:  Daria Kurandina; Padon Chuentragool; Vladimir Gevorgyan
Journal:  Synthesis (Stuttg)       Date:  2019-02-07       Impact factor: 3.157

5.  Enantiospecific intramolecular Heck reactions of secondary benzylic ethers.

Authors:  Michael R Harris; Mikhail O Konev; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2014-05-23       Impact factor: 15.419

6.  Palladium-Catalyzed Cross-Coupling of α-Bromocarbonyls and Allylic Alcohols for the Synthesis of α-Aryl Dicarbonyl Compounds.

Authors:  Yang Yu; Uttam K Tambar
Journal:  Chem Sci       Date:  2015       Impact factor: 9.825

7.  Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction.

Authors:  Marina Rubina; William M Sherrill; Alexey Yu Barkov; Michael Rubin
Journal:  Beilstein J Org Chem       Date:  2014-07-07       Impact factor: 2.883

8.  Introducing unactivated acyclic internal aliphatic olefins into a cobalt catalyzed allylic selective dehydrogenative Heck reaction.

Authors:  Soham Maity; Pravas Dolui; Rajesh Kancherla; Debabrata Maiti
Journal:  Chem Sci       Date:  2017-05-16       Impact factor: 9.825

9.  Water-soluble chiral tetrazine derivatives: towards the application of circularly polarized luminescence from upper-excited states to photodynamic therapy.

Authors:  Tingchao He; Can Ren; Yu Luo; Qi Wang; Junzi Li; Xiaodong Lin; Chuanxiang Ye; Wenbo Hu; Junmin Zhang
Journal:  Chem Sci       Date:  2019-03-08       Impact factor: 9.825

  9 in total

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