Prev. Article Next Article Table of Contents

Communication

The Ni-Mediated Cyclocarbonylation of Allyl Halides and Alkynes Made Catalytic. Evidence Supporting the Involvement of Pseudoradical Ni^I Species in the Mechanism

Supporting Info

M. Lluïsa Nadal, Julia Bosch, Josep M. Vila, Günter Klein, Susagna Ricart, and Josep M. Moretó*

Laboratori de Catlisi Homogenea, Institut de Cincia de Materials de Barcelona, (CSIC) Campus de la UAB, 08193 Bellaterra, Spain

J. Am. Chem. Soc., 2005, 127 (30), pp 10476–10477

DOI: 10.1021/ja0525713

Publication Date (Web): July 7, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, moreto@icmab.es

Abstract

We report here on a highly efficient catalytic method to synthesize intermolecularly the cyclopentane skeleton from starting products as simple as allyl halides, alkynes, and carbon monoxide under very mild reaction conditions by means of a substoichiometric amount of iron, acetone, and a catalytic amount of Ni(II) iodide.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue August 03, 2005
Received April 20, 2005

Recommend & Share

Related Content

Total Synthesis of (−)-Penifulvin A, an Insecticide with a Dioxafenestrane SkeletonJournal of the American Chemical Society
- Total Synthesis of (−)-Penifulvin A, an Insecticide with a Dioxafenestrane Skeleton
  Tanja Gaich and Johann Mulzer
  Journal of the American Chemical Society 2009 131 (2), pp 452–453
  Abstract: Herein we report the first total synthesis of Penifulvin A, a sesquiterpenoid with a novel dioxa-fenestrane structure. Penifulvin A is a potent insecticide against the fall armyworm Spodoptera frugiperda which causes enormous damage in the US by consuming ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Versatile Pd(II)-Catalyzed C−H Activation/Aryl−Aryl Coupling of Benzoic and Phenyl Acetic AcidsJournal of the American Chemical Society
- Versatile Pd(II)-Catalyzed C−H Activation/Aryl−Aryl Coupling of Benzoic and Phenyl Acetic Acids
  Dong-Hui Wang, Tian-Sheng Mei and Jin-Quan Yu
  Journal of the American Chemical Society 2008 130 (52), pp 17676–17677
  Abstract: The use of aryltrifluoroborates as coupling partners and O₂ as the oxidant substantially improves the scope and practicality of the Pd-catalyzed C−H activation/C−C coupling reaction. The newly discovered protocol made possible, for the first time, the ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Ruthenium-Catalyzed Cross-Coupling of Tertiary Propargyl Alcohols with ω-Alkynenitriles: A Regio- and Stereoselective Surrogate for an Aldol CondensationJournal of the American Chemical Society
- Ruthenium-Catalyzed Cross-Coupling of Tertiary Propargyl Alcohols with ω-Alkynenitriles: A Regio- and Stereoselective Surrogate for an Aldol Condensation
  Barry M. Trost, Nuno Maulide and Michael T. Rudd
  Journal of the American Chemical Society 2009 131 (2), pp 420–421
  Abstract: A novel catalytic alkyne cross-coupling reaction is reported which connects tertiary propargyl alcohols with ω-alkynylnitriles with perfect atom economy. This remarkable process generates highly functionalized, stereodefined dienones that are formal aldol ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

Communication

The Ni-Mediated Cyclocarbonylation of Allyl Halides and Alkynes Made Catalytic. Evidence Supporting the Involvement of Pseudoradical Ni^I Species in the Mechanism