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Title: Discovery and mechanistic investigation of Pt-catalyzed oxidative homocoupling of benzene with PhI(OAc) 2

Abstract

Pt-catalyzed direct coupling of benzene to biphenyl using PhI(OAc) 2 as an oxidant in the absence of any acid as a co-solvent or co-catalyst was mechanistically investigated.

Authors:
ORCiD logo [1]; ORCiD logo [2];  [3];  [3]; ORCiD logo [3]
  1. Professor Rashidi Laboratory of Organometallic Chemistry, Department of Chemistry, College of Sciences, Shiraz University, Iran
  2. Department of Chemistry, Shiraz Branch, Islamic Azad University, Shiraz 71993-37635, Iran
  3. Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1596173
Grant/Contract Number:  
SC0019161
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Dalton Transactions
Additional Journal Information:
Journal Name: Dalton Transactions Journal Volume: 49 Journal Issue: 8; Journal ID: ISSN 1477-9226
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Nabavizadeh, S. Masoud, Niroomand Hosseini, Fatemeh, Park, Chan, Wu, Guang, and Abu-Omar, Mahdi M. Discovery and mechanistic investigation of Pt-catalyzed oxidative homocoupling of benzene with PhI(OAc) 2. United Kingdom: N. p., 2020. Web. doi:10.1039/C9DT04261J.
Nabavizadeh, S. Masoud, Niroomand Hosseini, Fatemeh, Park, Chan, Wu, Guang, & Abu-Omar, Mahdi M. Discovery and mechanistic investigation of Pt-catalyzed oxidative homocoupling of benzene with PhI(OAc) 2. United Kingdom. doi:10.1039/C9DT04261J.
Nabavizadeh, S. Masoud, Niroomand Hosseini, Fatemeh, Park, Chan, Wu, Guang, and Abu-Omar, Mahdi M. Tue . "Discovery and mechanistic investigation of Pt-catalyzed oxidative homocoupling of benzene with PhI(OAc) 2". United Kingdom. doi:10.1039/C9DT04261J.
@article{osti_1596173,
title = {Discovery and mechanistic investigation of Pt-catalyzed oxidative homocoupling of benzene with PhI(OAc) 2},
author = {Nabavizadeh, S. Masoud and Niroomand Hosseini, Fatemeh and Park, Chan and Wu, Guang and Abu-Omar, Mahdi M.},
abstractNote = {Pt-catalyzed direct coupling of benzene to biphenyl using PhI(OAc) 2 as an oxidant in the absence of any acid as a co-solvent or co-catalyst was mechanistically investigated.},
doi = {10.1039/C9DT04261J},
journal = {Dalton Transactions},
number = 8,
volume = 49,
place = {United Kingdom},
year = {2020},
month = {2}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1039/C9DT04261J

Citation Metrics:
Cited by: 1 work
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Works referenced in this record:

Gold-catalyzed direct oxidative coupling reactions of non-activated arenes
journal, February 2009


Carbon–Oxygen Bond Forming Reductive Elimination from Cycloplatinated(IV) Complexes
journal, December 2017

  • Aseman, Marzieh Dadkhah; Nabavizadeh, S. Masoud; Niroomand Hosseini, Fatemeh
  • Organometallics, Vol. 37, Issue 1
  • DOI: 10.1021/acs.organomet.7b00745

Au-Catalyzed Cross-Coupling of Arenes via Double C–H Activation
journal, December 2015

  • Cambeiro, Xacobe C.; Ahlsten, Nanna; Larrosa, Igor
  • Journal of the American Chemical Society, Vol. 137, Issue 50
  • DOI: 10.1021/jacs.5b10593

Aerobic Oxidative Coupling of o-Xylene: Discovery of 2-Fluoropyridine as a Ligand to Support Selective Pd-Catalyzed CH Functionalization
journal, December 2010

  • Izawa, Yusuke; Stahl, Shannon S.
  • Advanced Synthesis & Catalysis, Vol. 352, Issue 18
  • DOI: 10.1002/adsc.201000771

Ru-Catalyzed C–H Arylation of Fluoroarenes with Aryl Halides
journal, March 2016

  • Simonetti, Marco; Perry, Gregory J. P.; Cambeiro, Xacobe C.
  • Journal of the American Chemical Society, Vol. 138, Issue 10
  • DOI: 10.1021/jacs.6b01615

Reaction Mechanisms of Mononuclear Non-Heme Iron Oxygenases
journal, June 2005

  • Abu-Omar, Mahdi M.; Loaiza, Aristobulo; Hontzeas, Nikos
  • Chemical Reviews, Vol. 105, Issue 6
  • DOI: 10.1021/cr040653o

Cyclometalation Using d-Block Transition Metals: Fundamental Aspects and Recent Trends
journal, February 2010


Pd-Catalyzed Aerobic Oxidative Coupling of Arenes: Evidence for Transmetalation between Two Pd(II)-Aryl Intermediates
journal, June 2014

  • Wang, Dian; Izawa, Yusuke; Stahl, Shannon S.
  • Journal of the American Chemical Society, Vol. 136, Issue 28
  • DOI: 10.1021/ja505405u

Mechanism of the Palladium-Catalyzed Arene C–H Acetoxylation: A Comparison of Catalysts and Ligand Effects
journal, February 2015

  • Cook, Amanda K.; Sanford, Melanie S.
  • Journal of the American Chemical Society, Vol. 137, Issue 8
  • DOI: 10.1021/jacs.5b00238

C–H reductive elimination during the reaction of cycloplatinated( ii ) complexes with pyridine-2-thione: kinetic follow up
journal, January 2015

  • Aseman, Marzieh Dadkhah; Nabavizadeh, S. Masoud; Shahsavari, Hamid R.
  • RSC Advances, Vol. 5, Issue 29
  • DOI: 10.1039/C5RA01341K

Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg
journal, January 1985

  • Hay, P. Jeffrey; Wadt, Willard R.
  • The Journal of Chemical Physics, Vol. 82, Issue 1
  • DOI: 10.1063/1.448799

A polyoxometalate-based PdII-coordinated ionic solid catalyst for heterogeneous aerobic oxidation of benzene to biphenyl
journal, January 2012

  • Zhao, Pingping; Leng, Yan; Zhang, Mingjue
  • Chemical Communications, Vol. 48, Issue 46
  • DOI: 10.1039/c2cc31919e

Double Deprotonation of Pyridinols Generates Potent Organic Electron-Donor Initiators for Haloarene-Arene Coupling
journal, March 2016

  • Barham, Joshua P.; Coulthard, Graeme; Kane, Ryan G.
  • Angewandte Chemie International Edition, Vol. 55, Issue 14
  • DOI: 10.1002/anie.201511847

Ruthenium-Catalyzed Oxidative Homo-Coupling of 2-Arylpyridines
journal, September 2009

  • Guo, Xiangyu; Deng, Guojun; Li, Chao-Jun
  • Advanced Synthesis & Catalysis, Vol. 351, Issue 13
  • DOI: 10.1002/adsc.200900375

Mechanism of Me–Re Bond Addition to Platinum(II) and Dioxygen Activation by the Resulting Pt–Re Bimetallic Center
journal, February 2017


Selective Aryl-Fluoride Reductive Elimination from a Platinum(IV) Complex
journal, June 2015

  • Dubinsky-Davidchik, Ina; Goldberg, Israel; Vigalok, Arkadi
  • Angewandte Chemie International Edition, Vol. 54, Issue 42
  • DOI: 10.1002/anie.201503116

Transition metal-catalysed couplings between arenes and strained or reactive rings: combination of C–H activation and ring scission
journal, January 2016

  • Wang, Fen; Yu, Songjie; Li, Xingwei
  • Chemical Society Reviews, Vol. 45, Issue 23
  • DOI: 10.1039/C6CS00371K

Synthesis of Biaryls through Aromatic CH Bond Activation: A Review of Recent Developments
journal, May 2014


Mechanistic Insights on Pd/Cu-Catalyzed Dehydrogenative Coupling of Dimethyl Phthalate
journal, May 2018


Oxidative C–H/C–H Coupling Reactions between Two (Hetero)arenes
journal, January 2017


Platinum-Catalyzed C–H Functionalization
journal, October 2016


A general gold-catalyzed direct oxidative coupling of non-activated arenes
journal, January 2008

  • Kar, Anirban; Mangu, Naveenkumar; Kaiser, Hanns Martin
  • Chem. Commun., Issue 3
  • DOI: 10.1039/B714928J

Pd-Catalyzed Aerobic Oxidative Biaryl Coupling: Non-Redox Cocatalysis by Cu(OTf) 2 and Discovery of Fe(OTf) 3 as a Highly Effective Cocatalyst
journal, April 2017

  • Wang, Dian; Stahl, Shannon S.
  • Journal of the American Chemical Society, Vol. 139, Issue 16
  • DOI: 10.1021/jacs.7b01970

Arene C–H bond activation and methane formation by a methylplatinum( ii ) complex: experimental and theoretical elucidation of the mechanism
journal, January 2019

  • Nahaei, Asma; Nabavizadeh, S. Masoud; Hosseini, Fatemeh Niroomand
  • New Journal of Chemistry, Vol. 43, Issue 21
  • DOI: 10.1039/C9NJ01968E

Cross-coupling of arene–gold(III) complexes
journal, July 2013


Ligand-Promoted Direct C–H Arylation of Simple Arenes: Evidence for a Cooperative Bimetallic Mechanism
journal, April 2017


Platinum-Catalyzed C–H Arylation of Simple Arenes
journal, October 2013

  • Wagner, Anna M.; Hickman, Amanda J.; Sanford, Melanie S.
  • Journal of the American Chemical Society, Vol. 135, Issue 42
  • DOI: 10.1021/ja408112j

Highly Active Palladium-Based Catalyst System for the Aerobic Oxidative Direct Coupling of Benzene to Biphenyl
journal, November 2015


Over-Oxidation as the Key Step in the Mechanism of the MoCl 5 -Mediated Dehydrogenative Coupling of Arenes
journal, October 2015

  • Schubert, Moritz; Franzmann, Peter; Wünsche von Leupoldt, Anica
  • Angewandte Chemie International Edition, Vol. 55, Issue 3
  • DOI: 10.1002/anie.201508035

Assembly of Cyclometalated Platinum(II) Complexes via 1,1′-Bis(diphenylphosphino)ferrocene Ligand: Kinetics and Mechanisms
journal, March 2011

  • Nabavizadeh, S. Masoud; Amini, Hashem; Shahsavari, Hamid R.
  • Organometallics, Vol. 30, Issue 6
  • DOI: 10.1021/om101055n

A residue-free production of biaryls using supported gold nanoparticles
journal, June 2014


Kinetico-mechanistic studies on CX (X=H, F, Cl, Br, I) bond activation reactions on organoplatinum(II) complexes
journal, November 2014

  • Crespo, Margarita; Martínez, Manuel; Nabavizadeh, S. Masoud
  • Coordination Chemistry Reviews, Vol. 279
  • DOI: 10.1016/j.ccr.2014.06.010

C–H Functionalization at Sterically Congested Positions by the Platinum-Catalyzed Borylation of Arenes
journal, September 2015

  • Furukawa, Takayuki; Tobisu, Mamoru; Chatani, Naoto
  • Journal of the American Chemical Society, Vol. 137, Issue 38
  • DOI: 10.1021/jacs.5b07677

Stable organoplatinum complexes as intermediates and models in hydrocarbon functionalization
journal, September 2015