Literature DB >> 11856003

Nickel-catalyzed intermolecular coupling of 1,3-dienes and aldehydes via transmetalation of nickelacycles with diisobutylaluminum acetylacetonate.

Yoshihiro Sato1, Rieko Sawaki, Nozomi Saito, Miwako Mori.   

Abstract

Intermolecular coupling reactions of 1,3-dienes and aldehydes via transmetalation of nickelacycle intermediate with (i)Bu(2)Al-acac were investigated. In the reactions, a linear adduct or a branched adduct was produced, depending upon the nature of 1,3-dienes and aldehydes, via two nickelacycles that were relatively stable among the four possible nickelacycles because of the equilibrium with pi-allynickel forms.

Entities:  

Year:  2002        PMID: 11856003     DOI: 10.1021/jo0106086

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  12 in total

Review 1.  Catalytic carbonyl addition through transfer hydrogenation: a departure from preformed organometallic reagents.

Authors:  John F Bower; In Su Kim; Ryan L Patman; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  Ni-catalyzed borylative diene-aldehyde coupling: the remarkable effect of P(SiMe3)3.

Authors:  Hee Yeon Cho; James P Morken
Journal:  J Am Chem Soc       Date:  2010-06-09       Impact factor: 15.419

3.  Formation of C-C Bonds via Ruthenium Catalyzed Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level.

Authors:  Fumitoshi Shibahara; Michael J Krische
Journal:  Chem Lett       Date:  2008       Impact factor: 1.389

4.  Stereoselective borylative ketone-diene coupling.

Authors:  Hee Yeon Cho; Zhiyong Yu; James P Morken
Journal:  Org Lett       Date:  2011-09-12       Impact factor: 6.005

5.  Direct ruthenium-catalyzed C-C coupling of ethanol: diene hydro-hydroxyethylation to form all-carbon quaternary centers.

Authors:  Hoon Han; Michael J Krische
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

6.  Diastereoselective construction of functionalized homoallylic alcohols by Ni-catalyzed diboron-promoted coupling of dienes and aldehydes.

Authors:  Hee Yeon Cho; James P Morken
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

7.  Ruthenium-catalyzed C-C bond forming transfer hydrogenation: carbonyl allylation from the alcohol or aldehyde oxidation level employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents.

Authors:  Fumitoshi Shibahara; John F Bower; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-04-29       Impact factor: 15.419

8.  Direct, redox-neutral prenylation and geranylation of secondary carbinol C-H bonds: C4-regioselectivity in ruthenium-catalyzed C-C couplings of dienes to α-hydroxy esters.

Authors:  Joyce C Leung; Laina M Geary; Te-Yu Chen; Jason R Zbieg; Michael J Krische
Journal:  J Am Chem Soc       Date:  2012-09-17       Impact factor: 15.419

9.  Regioselective ruthenium catalyzed hydrohydroxyalkylation of dienes with 3-hydroxy-2-oxindoles: prenylation, geranylation, and beyond.

Authors:  Te-Yu Chen; Michael J Krische
Journal:  Org Lett       Date:  2013-05-30       Impact factor: 6.005

Review 10.  Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Authors:  Michael Holmes; Leyah A Schwartz; Michael J Krische
Journal:  Chem Rev       Date:  2018-06-13       Impact factor: 60.622

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