Literature DB >> 30698952

Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations.

Rachel Trammell1, Khashayar Rajabimoghadam1, Isaac Garcia-Bosch1.   

Abstract

Copper is one of the most abundant and less toclass="Chemical">n>an class="Chemical">xic transition metals. Nature takes advantage of the bioavailability and rich redox chemistry of Cu to carry out oxygenase and oxidase organic transformations using O2 (or H2O2) as oxidant. Inspired by the reactivity of these Cu-dependent metalloenzymes, chemists have developed synthetic protocols to functionalize organic molecules under enviormentally benign conditions. Copper also promotes other transformations usually catalyzed by 4d and 5d transition metals (Pd, Pt, Rh, etc.) such as nitrene insertions or C-C and C-heteroatom coupling reactions. In this review, we summarized the most relevant research in which copper promotes or catalyzes the functionalization of organic molecules, including biological catalysis, bioinspired model systems, and organometallic reactivity. The reaction mechanisms by which these processes take place are discussed in detail.

Entities:  

Mesh:

Substances:

Year:  2019        PMID: 30698952      PMCID: PMC6571019          DOI: 10.1021/acs.chemrev.8b00368

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  332 in total

1.  Oxygenation of phenols to catechols by a (mu-eta 2:eta 2-peroxo)dicopper(II) complex: mechanistic insight into the phenolase activity of tyrosinase.

Authors:  S Itoh; H Kumei; M Taki; S Nagatomo; T Kitagawa; S Fukuzumi
Journal:  J Am Chem Soc       Date:  2001-07-11       Impact factor: 15.419

2.  C-H bond activation of external substrates with a bis(mu-oxo)dicopper(III) complex.

Authors:  M Taki; S Itoh; S Fukuzumi
Journal:  J Am Chem Soc       Date:  2001-06-27       Impact factor: 15.419

3.  Mechanisms Whereby Mononuclear Copper Proteins Functionalize Organic Substrates.

Authors:  Judith P. Klinman
Journal:  Chem Rev       Date:  1996-11-07       Impact factor: 60.622

4.  Aryl CbondH activation by CuII to form an organometallic aryl-CuIII species: a novel twist on copper disproportionation.

Authors:  Xavi Ribas; Deanne A Jackson; Bruno Donnadieu; José Mahía; Teodor Parella; Raül Xifra; Britt Hedman; Keith O Hodgson; Antoni Llobet; T Daniel P Stack
Journal:  Angew Chem Int Ed Engl       Date:  2002-08-16       Impact factor: 15.336

5.  Aliphatic Hydroxylation by a Bis(µ-oxo)dicopper(III) Complex.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-01       Impact factor: 15.336

6.  Reversible dioxygen binding and phenol oxygenation in a tyrosinase model system.

Authors:  L Santagostini; M Gullotti; E Monzani; L Casella; R Dillinger; F Tuczek
Journal:  Chemistry       Date:  2000-02-04       Impact factor: 5.236

7.  Synthesis, structure, and H2O2-dependent catalytic functions of disulfide-bridged dicopper(I) and related thioether-copper(I) and thioether-copper(II) complexes.

Authors:  T Ohta; T Tachiyama; K Yoshizawa; T Yamabe; T Uchida; T Kitagawa
Journal:  Inorg Chem       Date:  2000-09-18       Impact factor: 5.165

Review 8.  A critical overview of the chemistry of copper-dependent low density lipoprotein oxidation: roles of lipid hydroperoxides, alpha-tocopherol, thiols, and ceruloplasmin.

Authors:  M J Burkitt
Journal:  Arch Biochem Biophys       Date:  2001-10-01       Impact factor: 4.013

9.  Contrasting copper-dioxygen chemistry arising from alike tridentate alkyltriamine copper(I) complexes.

Authors:  Hong-Chang Liang; Christiana Xin Zhang; Mark J Henson; Roger D Sommer; Karen R Hatwell; Susan Kaderli; Andreas D Zuberbühler; Arnold L Rheingold; Edward I Solomon; Kenneth D Karlin
Journal:  J Am Chem Soc       Date:  2002-04-24       Impact factor: 15.419

10.  Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes.

Authors:  X Li; J Yang; M C Kozlowski
Journal:  Org Lett       Date:  2001-04-19       Impact factor: 6.005

View more
  18 in total

1.  Impact of Intramolecular Hydrogen Bonding on the Reactivity of Cupric Superoxide Complexes with O-H and C-H Substrates.

Authors:  Daniel E Diaz; David A Quist; Austin E Herzog; Andrew W Schaefer; Ioannis Kipouros; Mayukh Bhadra; Edward I Solomon; Kenneth D Karlin
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-23       Impact factor: 15.336

2.  Mononuclear and Dinuclear Copper Complexes of Tridentate Redox-active Ligands with Tunable H-bonding Donors: Structure, Spectroscopy and H+ /e- Reactivity.

Authors:  Tong Wu; Justin Musgrove; Maxime A Siegler; Isaac Garcia-Bosch
Journal:  Chem Asian J       Date:  2021-05-13

Review 3.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Authors:  Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal:  Chem Rev       Date:  2021-10-29       Impact factor: 60.622

4.  Practical One-Pot Multistep Synthesis of 2H-1,3-Benzoxazines Using Copper, Hydrogen Peroxide and Triethylamine.

Authors:  Rachel Trammell; Alexandra Cordova; Shuming Zhang; Sunipa Goswami; Richel Murata; Maxime A Siegler; Isaac Garcia-Bosch
Journal:  European J Org Chem       Date:  2021-08-17

5.  Reversible Scavenging of Dioxygen from Air by a Copper Complex.

Authors:  Kurtis M Carsch; Andrei Iliescu; Ryan D McGillicuddy; Jarad A Mason; Theodore A Betley
Journal:  J Am Chem Soc       Date:  2021-10-21       Impact factor: 16.383

6.  Enantioselective, Aerobic Copper-Catalyzed Intramolecular Carboamination and Carboetherification of Unactivated Alkenes.

Authors:  Tomasz Wdowik; Samuel L Galster; Raul L L Carmo; Sherry R Chemler
Journal:  ACS Catal       Date:  2020-07-16       Impact factor: 13.084

7.  Structure, Spectroscopy, and Reactivity of a Mononuclear Copper Hydroxide Complex in Three Molecular Oxidation States.

Authors:  Tong Wu; Samantha N MacMillan; Khashayar Rajabimoghadam; Maxime A Siegler; Kyle M Lancaster; Isaac Garcia-Bosch
Journal:  J Am Chem Soc       Date:  2020-07-01       Impact factor: 15.419

8.  Structural Characterization of the [CuOR]2+ Core.

Authors:  V Mahesh Krishnan; Dimitar Y Shopov; Caitlin J Bouchey; Wilson D Bailey; Riffat Parveen; Bess Vlaisavljevich; William B Tolman
Journal:  J Am Chem Soc       Date:  2021-02-23       Impact factor: 15.419

9.  Sulfur-Containing Analogues of the Reactive [CuOH]2+ Core.

Authors:  Wen Wu; Jacqui Tehranchi De Hont; Riffat Parveen; Bess Vlaisavljevich; William B Tolman
Journal:  Inorg Chem       Date:  2021-03-18       Impact factor: 5.165

10.  Cross dehydrogenative C-O coupling catalysed by a catenane-coordinated copper(i).

Authors:  Lihui Zhu; Jiasheng Li; Jun Yang; Ho Yu Au-Yeung
Journal:  Chem Sci       Date:  2020-11-01       Impact factor: 9.825

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.