Literature DB >> 22040103

Gaining absolute control of the regiochemistry in the cobalt-catalyzed 1,4-hydrovinylation reaction.

Marion Arndt1, Mehmet Dindaroğlu, Hans-Günther Schmalz, Gerhard Hilt.   

Abstract

The absolute control of the regiochemistry of a cobalt-catalyzed 1,4-hydrovinylation reaction is achieved by alternation of the ligands applied. While the dppe/dppp ligands led to the formation of the branched product, the herein described application of the SchmalzPhos ligand generates the corresponding linear product in both excellent yields and regioselectivities. The catalyst system exhibits a high tolerance toward functional groups, and the very mild reaction conditions allow the synthesis of 1,4-dienes without isomerization into conjugated systems.

Entities:  

Year:  2011        PMID: 22040103     DOI: 10.1021/ol202696n

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


  9 in total

1.  Asymmetric hydrovinylation of 1-vinylcycloalkenes. Reagent control of regio- and stereoselectivity.

Authors:  Jordan P Page; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2012-03-30       Impact factor: 15.419

2.  Pyridine(diimine) Iron Diene Complexes Relevant to Catalytic [2+2]-Cycloaddition Reactions.

Authors:  C Rose Kennedy; Hongyu Zhong; Matthew V Joannou; Paul J Chirik
Journal:  Adv Synth Catal       Date:  2019-11-19       Impact factor: 5.837

3.  Activator-free single-component Co(I)-catalysts for regio- and enantioselective heterodimerization and hydroacylation reactions of 1,3-dienes. New reduction procedures for synthesis of [L]Co(I)-complexes and comparison to in situ generated catalysts.

Authors:  Mahesh M Parsutkar; Curtis E Moore; T V RajanBabu
Journal:  Dalton Trans       Date:  2022-07-05       Impact factor: 4.569

4.  Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

Authors:  Matthew S McCammant; Longyan Liao; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2013-03-12       Impact factor: 15.419

5.  Selective [1,4]-Hydrovinylation of 1,3-Dienes with Unactivated Olefins Enabled by Iron Diimine Catalysts.

Authors:  Valerie A Schmidt; C Rose Kennedy; Máté J Bezdek; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2018-02-21       Impact factor: 15.419

6.  Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes.

Authors:  Philipp Röse; Steffen Emge; Jun-Ichi Yoshida; Gerhard Hilt
Journal:  Beilstein J Org Chem       Date:  2015-01-28       Impact factor: 2.883

7.  Cobalt-Catalysed Asymmetric Hydrovinylation of 1,3-Dienes.

Authors:  Yam N Timsina; Rakesh K Sharma; T V RajanBabu
Journal:  Chem Sci       Date:  2015-04-23       Impact factor: 9.825

8.  Unpredictable cycloisomerization of 1,11-dien-6-ynes by a common cobalt catalyst.

Authors:  Abdusalom A Suleymanov; Dmitry V Vasilyev; Valentin V Novikov; Yulia V Nelyubina; Dmitry S Perekalin
Journal:  Beilstein J Org Chem       Date:  2017-03-31       Impact factor: 2.883

9.  Regioselective hydroacylation of 1,3-dienes by cobalt catalysis.

Authors:  Qing-An Chen; Daniel K Kim; Vy M Dong
Journal:  J Am Chem Soc       Date:  2014-03-03       Impact factor: 15.419

  9 in total

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