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Author : Marcela Wanderley
Publisher :
Page : 82 pages
File Size : 15,37 MB
Release : 2009
Category : Copper catalysts
ISBN :
Author : Gergely Sirokman
Publisher :
Page : 198 pages
File Size : 23,44 MB
Release : 2007
Category :
ISBN :
This thesis presents work towards the development of a new catalytic C-C bond forming reaction. Alkynes and olefins insert into [(IPr)CuH]2 (IPr = N, N-bis-(2,6-diisopropylphenyl)-1,3-imidazol-2-ylidene) to give copper vinyl and copper alkyl complexes. These copper complexes insert CO2 into the Cu-C bond to form copper acrylate and copper carboxylate complexes. Acrylic and carboxylic acids can be isolated by hydrolysis. A catalytic cycle based on (IPr)copper(I) was developed. Alkynes undergo reductive carboxylation to give acrylic acids in moderate yields. Unexpected interactions between several components of the catalytic system led to a number of side reaction, most importantly between [(IPr)CuH]2 and the product silyl acrylate. The use of silylcarbonate salts to desylilate the product enhanced yield. In addition, silylcarbonates can also serve as a source of CO2.
Author : Akkattu T. Biju
Publisher : John Wiley & Sons
Page : 407 pages
File Size : 20,81 MB
Release : 2019-01-07
Category : Science
ISBN : 3527809058
Summarizing the emerging field of N-heterocyclic carbenes used in organocatalysis, this is an excellent overview of the synthesis and applications of NHCs focusing on carbon-carbon and carbon-heteroatom bond formation. Alongside comprehensive coverage of the synthesis, characteristics and applications, this handbook and ready reference also includes chapters on NHCs for polymerization reactions and natural product synthesis.
Author : Ananya Srivastava
Publisher : Elsevier
Page : 506 pages
File Size : 18,5 MB
Release : 2020-11-13
Category : Science
ISBN : 012821547X
Copper in N-Heterocyclic Chemistry provides an overview of copper-catalyzed synthesis and functionalization of N-heterocyclic compounds, covering all recent developments in a way that is ideal for researchers and students working in the area of synthetic organic chemistry and medicinal chemistry. The book explores N-heterocyclic compounds as unique structural units in the development of natural products and pharmaceuticals, along with the remarkable progress made in the area of high atom economic strategies, and more recently, copper-catalyzed C-H activation and its applications in organic synthesis. Readers will find troubleshooting protocols, as well as the advantages and limitations of each method discussed. As copper catalysts show versatile chemical reactivity in many aspects, including their oxidation states 0–3 are accessible and their ability to facilitate bond formations due to their ability to serve as Lewis acids, oxidizing agents and catalysts, this book is an ideal resource on the topics explored. Discusses novel synthetic methods developed over the past decade for copper-catalyzed synthesis of N-heterocyclic compounds Covers the most recent methodologies adapted in synthetic chemistry for applications in natural products and pharmaceuticals Includes troubleshooting protocols, as well as the advantages and limitations of each method discussed in detail
Author : James David Cope
Publisher :
Page : 273 pages
File Size : 14,92 MB
Release : 2020
Category :
ISBN :
Development of C–N bond formation chemistry is a continuing field of study. Recently copper based Chan-Evans-Lam cross-coupling was discovered, and although our understanding of the mechanism has grown, there are still many unanswered questions to be explored. Herein, we set out to develop a series of copper complexes that can stabilize different oxidation states in an attempt to probe how this impacts the mechanism. Initially complexes of copper(II) with 1,10 phenanthroline (phen) and related ligands were generated for use with CEL coupling. The complexes were probed electrochemically and photophysically and found that the 4,5-diazafluorenone complex 4 had a Cu2+/Cu+ potential +1.1 V relative to phen. We observed that the copper complex 4, which stabilize the Cu+, gave the greatest yield of the desired product. Following this study, we aimed to synthesize novel N-heterocyclic carbene copper complexes, which could better stabilize the copper(II) and copper(III) states. Several ligands and derivatives were synthesized, and copper(II) complexes were made using Cu(OAc)2 as a direct metalation agent. This complex was characterized via several spectroscopic methods and it was found to be a copper(II) complex. Initially this complex was thought to be relatively air stable but it was found to slowly decomposed to a novel di-copper bis-imidazolium complex over the course of 96 hours. While the identity of some of the intermediates are unknown, crystals of a potential end point were grown. A series of preliminary C–N coupling reactions show that the NHC copper(II) complexes are possible catalysts in alcoholic solvents.
Author : Steven P. Nolan
Publisher : John Wiley & Sons
Page : 319 pages
File Size : 38,36 MB
Release : 2006-12-13
Category : Science
ISBN : 3527609407
This first handbook to focus solely on the application of N-heterocyclic carbenes in synthesis covers metathesis, organocatalysis, oxidation and asymmetric reactions, along with experimental procedures. Written by leading international experts this is a valuable and practical source for every organic chemist.
Author : Silvia Diez-Gonzalez
Publisher : Royal Society of Chemistry
Page : 637 pages
File Size : 14,56 MB
Release : 2016-11-04
Category : Science
ISBN : 1782626816
In less than 20 years N-heterocyclic carbenes (NHCs) have become well-established ancillary ligands for the preparation of transition metal-based catalysts. This is mainly due to the fact that NHCs tend to bind strongly to metal centres, avoiding the need of excess ligand in catalytic reactions. Also, NHC‒metal complexes are often insensitive to air and moisture, and have proven remarkably resistant to oxidation. This book showcases the wide variety of applications of NHCs in different chemistry fields beyond being simple phosphine mimics. This second edition has been updated throughout, and now includes a new chapter on NHC‒main group element complexes. It covers the synthesis of NHC ligands and their corresponding metal complexes, as well as their bonding and stereoelectronic properties and applications in catalysis. This is complemented by related topics such as organocatalysis and biologically active complexes. Written for organic and inorganic chemists, this book is ideal for postgraduates, researchers and industrialists.
Author : Steven P. Nolan
Publisher : John Wiley & Sons
Page : 690 pages
File Size : 36,52 MB
Release : 2014-07-07
Category : Science
ISBN : 3527671242
This comprehensive reference and handbook covers in depth all major aspects of the use of N-heterocyclic carbene-complexes in organic synthesis: from the theoretical background to characterization, and from cross-coupling reactions to olefin metathesis. Edited by a leader and experienced scientist in the field of homogeneous catalysis and use of NHCs, this is an essential tool for every academic and industrial synthetic chemist.
Author : Tatiana Le Gall
Publisher :
Page : pages
File Size : 48,4 MB
Release : 2011
Category :
ISBN :
Author : David Stephen Laitar
Publisher :
Page : 216 pages
File Size : 32,80 MB
Release : 2006
Category :
ISBN :
(Cont.) Carbon dioxide also inserts into the Cu-Si bond of a copper silyl complex. The resulting complex evolves CO to give a copper siloxide complex. Mesitaldehyde inserts cleanly and selectively into the Cu-B bond of (NHC)CuB(pin), to form a B-O and a copper-carbon bond. This complex reacts with bis(pinacolato)diboron to regenerate (NHC)CuB(pin) and produce an aldehyde diboration product, in which a diboron reagent has been added across the C=O bond of mesitaldehyde. A copper boryl complex with a smaller NHC supporting ligand proved to be a much more effective diboration catalyst and a wide range of aldehydes react cleanly with bis(pinacolato)diboron. The insertion of alkenes into an (NHC)copper(I) boryl affords isolable -boroalkyl complexes in high yields; competition experiments using substituted styrenes show that electron-donating substituents slow the reaction. Although the insertion products are stable at ambient temperature, a P-hydride elimination/reinsertion sequence affords a rearranged a-boroalkyl complex on heating.