Literature DB >> 26120214

Surprisingly Facile C-H Activation in the Course of Oxime-Directed Catalytic Asymmetric Hydroboration.

Nathan C Thacker1, Veronika M Shoba1, Andrew E Geis1, James M Takacs1.   

Abstract

Deuterium-labeling studies carried out in conjunction with investigations into the directed catalytic asymmetric hydroboration of unsaturated oxime ethers reveal a surprisingly facile ortho-metallation or σ-bond metathesis pathway that that diverts the expected course of CAHB to a tandem C-H activation/hydroboration reaction pathway.

Entities:  

Keywords:  C-H activation; directed metallation; rhodium-catalyzed borylation; rhodium-catalyzed hydroboration

Year:  2015        PMID： 26120214      PMCID： PMC4480785          DOI： 10.1016/j.tetlet.2014.12.076

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  34 in total

1.  Rh(III)-catalyzed dual directing group assisted sterically hindered C-H bond activation: a unique route to meta and ortho substituted benzofurans.

Authors:  Chien-Hung Yeh; Wei-Chen Chen; Parthasarathy Gandeepan; Ya-Chun Hong; Cheng-Hung Shih; Chien-Hong Cheng
Journal:  Org Biomol Chem       Date:  2014-12-07       Impact factor: 3.876

2.  Catalytic asymmetric hydroboration of β,γ-unsaturated Weinreb amides: striking influence of the borane.

Authors:  Sean M Smith; Maulen Uteuliyev; James M Takacs
Journal:  Chem Commun (Camb)       Date:  2011-06-03       Impact factor: 6.222

3.  TADDOL-derived phosphites and phosphoramidites for efficient rhodium-catalyzed asymmetric hydroboration.

Authors:  Shin A Moteki; Di Wu; Kusum L Chandra; D Sahadeva Reddy; James M Takacs
Journal:  Org Lett       Date:  2006-07-06       Impact factor: 6.005

4.  γ-Selective directed catalytic asymmetric hydroboration of 1,1-disubstituted alkenes.

Authors:  Sean M Smith; Gia L Hoang; Rhitankar Pal; Mohammad O Bani Khaled; Liberty S W Pelter; Xiao Cheng Zeng; James M Takacs
Journal:  Chem Commun (Camb)       Date:  2012-12-28       Impact factor: 6.222

5.  Palladium-Catalyzed Ligand-Directed Oxidative Functionalization of Cyclopropanes.

Authors:  Asako Kubota; Melanie S Sanford
Journal:  Synthesis (Stuttg)       Date:  2011-08       Impact factor: 3.157

6.  Pd-catalyzed ortho-C-H acylation/cross coupling of aryl ketone O-methyl oximes with aldehydes using tert-butyl hydroperoxide as oxidant.

Authors:  Chun-Wo Chan; Zhongyuan Zhou; Albert S C Chan; Wing-Yiu Yu
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

7.  The sigma-CAM Mechanism: sigma complexes as the basis of sigma-bond metathesis at late-transition-metal centers.

Authors:  Robin N Perutz; Sylviane Sabo-Etienne
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

8.  Amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes.

Authors:  Sean M Smith; James M Takacs
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

9.  Efficient amide-directed catalytic asymmetric hydroboration.

Authors:  Sean M Smith; Nathan C Thacker; James M Takacs
Journal:  J Am Chem Soc       Date:  2008-03-01       Impact factor: 15.419

10.  Mechanistic Insights into Carbonyl-Directed Rhodium-Catalyzed Hydroboration: ab Initio Study of a Cyclic γ,δ-Unsaturated Amide.

Authors:  Zhao-Di Yang; Rhitankar Pal; Gia L Hoang; Xiao Cheng Zeng; James M Takacs
Journal:  ACS Catal       Date:  2014-01-22       Impact factor: 13.084
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  1 in total

1.  Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration.

Authors:  Veronika M Shoba; Nathan C Thacker; Andrew J Bochat; James M Takacs
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-10       Impact factor: 15.336
  1 in total

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