Literature DB >> 18389129

Nickeladihydrofuran. Key intermediate for nickel-catalyzed reaction of alkyne and aldehyde.

Sensuke Ogoshi1, Tomoya Arai, Masato Ohashi, Hideo Kurosawa.   

Abstract

The formation of a nickeladihydrofuran by oxidative cyclization of an alkyne and an aldehyde with nickel(0) has been demonstrated; the transformation of the nickeladihydrofuran into an enone by decomposition, a lactone by carbonylation and an allylic alcohol by treatment with ZnMe(2) suggests that nickeladihydrofuran is an important key intermediate in a variety of catalytic reactions.

Entities:  

Year:  2008        PMID： 18389129     DOI： 10.1039/b717261c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  15 in total

1.  Synthesis of Tetrasubstituted Alkenes by Tandem Metallacycle Formation/Cross-Electrophile Coupling.

Authors:  Kirk W Shimkin; John Montgomery
Journal:  J Am Chem Soc       Date:  2018-05-31       Impact factor: 15.419

2.  NHC Ligands Tailored for Simultaneous Regio- and Enantiocontrol in Nickel-Catalyzed Reductive Couplings.

Authors:  Hengbin Wang; Gang Lu; Grant J Sormunen; Hasnain A Malik; Peng Liu; John Montgomery
Journal:  J Am Chem Soc       Date:  2017-07-03       Impact factor: 15.419

3.  Redox-triggered C-C coupling of diols and alkynes: synthesis of β,γ-unsaturated α-hydroxyketones and furans by ruthenium-catalyzed hydrohydroxyalkylation.

Authors:  Emma L McInturff; Khoa D Nguyen; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-17       Impact factor: 15.336

4.  Mechanistic Basis for Regioselection and Regiodivergence in Nickel-Catalyzed Reductive Couplings.

Authors:  Evan P Jackson; Hasnain A Malik; Grant J Sormunen; Ryan D Baxter; Peng Liu; Hengbin Wang; Abdur-Rafay Shareef; John Montgomery
Journal:  Acc Chem Res       Date:  2015-05-12       Impact factor: 22.384

5.  Nickel-catalyzed dehydrogenative cross-coupling: direct transformation of aldehydes into esters and amides.

Authors:  Aaron M Whittaker; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-25       Impact factor: 15.336

6.  Mechanistic study of nickel-catalyzed ynal reductive cyclizations through kinetic analysis.

Authors:  Ryan D Baxter; John Montgomery
Journal:  J Am Chem Soc       Date:  2011-03-28       Impact factor: 15.419

7.  Masked Radicals: Iron Complexes of Trityl, Benzophenone, and Phenylacetylene.

Authors:  K Cory MacLeod; Ida M DiMucci; Edward P Zovinka; Sean F McWilliams; Brandon Q Mercado; Kyle M Lancaster; Patrick L Holland
Journal:  Organometallics       Date:  2019-10-10       Impact factor: 3.876

8.  Origins of regioselectivity and alkene-directing effects in nickel-catalyzed reductive couplings of alkynes and aldehydes.

Authors:  Peng Liu; Patrick McCarren; Paul Ha-Yeon Cheong; Timothy F Jamison; K N Houk
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

9.  Mechanism and transition-state structures for nickel-catalyzed reductive alkyne-aldehyde coupling reactions.

Authors:  P R McCarren; Peng Liu; Paul Ha-Yeon Cheong; Timothy F Jamison; K N Houk
Journal:  J Am Chem Soc       Date:  2009-05-20       Impact factor: 15.419

10.  Cooperativity of regiochemistry control strategies in reductive couplings of propargyl alcohols and aldehydes.

Authors:  Hasnain A Malik; Mani Raj Chaulagain; John Montgomery
Journal:  Org Lett       Date:  2009-12-17       Impact factor: 6.005
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