Title: Visible light-induced palladium–carbon bond weakening in catalytically relevant T-shaped complexes

Journal Article · · Chemical Science
DOI: https://doi.org/10.1039/D3SC02588H · OSTI ID:2222554

Triggering one-electron redox processes during palladium catalysis holds the potential to unlock new reaction mechanisms and synthetic methods not previously accessible in the typical two-electron reaction manifolds that dominate palladium catalysis.

Research Organization:
Princeton University, NJ (United States)
Sponsoring Organization:
USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB)
Grant/Contract Number:
SC0019370
OSTI ID:
2222554
Journal Information:
Chemical Science, Journal Name: Chemical Science Journal Issue: 48 Vol. 14; ISSN 2041-6520; ISSN CSHCBM
Publisher:
Royal Society of Chemistry (RSC)Copyright Statement
Country of Publication:
United Kingdom
Language:
English

References (130)

Phosphorescent Pt(II) and Pd(II) Complexes for Efficient, High-Color-Quality, and Stable OLEDs journal November 2016
Combining Transition Metal Catalysis with Radical Chemistry: Dramatic Acceleration of Palladium-Catalyzed CH Arylation with Diaryliodonium Salts journal December 2012
Ullmann‐Goldberg and Buchwald‐Hartwig C−N Cross Couplings: Synthetic Methods to Pharmaceutically Potential N‐Heterocycles journal April 2021
Monoligated Palladium Species as Catalysts in Cross-Coupling Reactions journal January 2005
Redox Reactions in Palladium Catalysis: On the Accelerating and/or Inhibiting Effects of Copper and Silver Salt Additives in Cross-Coupling Chemistry Involving Electron-rich Phosphine Ligands journal June 2012
Synthesis of Indoles Using Visible Light: Photoredox Catalysis for Palladium-Catalyzed CH Activation journal October 2014
Visible‐Light‐Driven Palladium‐Catalyzed Radical Alkylation of C−H Bonds with Unactivated Alkyl Bromides journal November 2017
Visible Light-Induced Room-Temperature Heck Reaction of Functionalized Alkyl Halides with Vinyl Arenes/Heteroarenes journal October 2017
Palladium‐Catalyzed Atom‐Transfer Radical Cyclization at Remote Unactivated C(sp3)−H Sites: Hydrogen‐Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates journal February 2018
Palladium‐Catalyzed para‐Selective Alkylation of Electron‐Deficient Arenes journal April 2018
Visible‐Light‐Induced Organic Photochemical Reactions through Energy‐Transfer Pathways journal December 2018
Photoinduced Palladium‐Catalyzed Negishi Cross‐Couplings Enabled by the Visible‐Light Absorption of Palladium–Zinc Complexes journal September 2018
Oxidative Addition to Palladium(0) Made Easy through Photoexcited-State Metal Catalysis: Experiment and Computation journal January 2019
Catalysis with Palladium Complexes Photoexcited by Visible Light journal May 2019
The Buchwald–Hartwig Amination After 25 Years journal November 2019
Catalysis with Palladium(I) Dimers journal December 2020
Regio‐, Diastereo‐, and Enantioselective Decarboxylative Hydroaminoalkylation of Dienol Ethers Enabled by Dual Palladium/Photoredox Catalysis journal March 2022
Zum Reaktionsmechanismus der photochemischen Bildung von Pentacarbonylmetallverbindungen M(CO)5D journal February 1961
Palladium‐Catalyzed Decarboxylative Heck‐Type Coupling of Activated Aliphatic Carboxylic Acids Enabled by Visible Light journal February 2018
Photoactive Nickel Complexes in Cross‐Coupling Catalysis journal November 2020
Development of Palladium Precatalysts that Efficiently Generate LPd(0) Active Species journal September 2019
Photoinitiated atom transfer radical polymerization: Current status and future perspectives journal August 2014
Visible‐Light Enabled Late‐Stage, Room‐Temperature Aminocarbonylation of Aryl Iodides with Labeled Carbon Monoxide journal December 2022
Luminescent Pd(II) Complexes with Tridentate − Aryl‐pyridine‐(benzo)thiazole Ligands journal November 2021
Photochemistry and Photophysics of Coordination Compounds: Ruthenium book January 2007
The life and times of excited states of organometallic and coordination compounds journal May 2000
Editorial journal October 1998
Reactivity studies of [Pd2(μ-X)2(PBut3)2] (X = Br, I) with CNR (R = 2,6-dimethylphenyl), H2 and alkynes journal April 2000
Photodecomposition of platinum and palladium alkyls: A cidnp study journal December 1977
Photochemical synthesis of a palladium dichloromethyl complex, {(hexyl)HC(N-methyl-imidazol-2-yl)2}Pd(CHCl2)Cl. journal October 2003
Energy Conversion in Natural and Artificial Photosynthesis journal May 2010
Buchwald-Hartwig reaction: An overview journal April 2018
Addition polymerization of functionalized norbornenes as a powerful tool for assembling molecular moieties of new polymers with versatile properties journal September 2018
Carboxylic Acids as Adaptive Functional Groups in Metallaphotoredox Catalysis journal November 2022
Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis journal November 2021
Halide Photoredox Chemistry journal March 2019
Solution Dynamics of Redox Noninnocent Nitrosoarene Ligands: Mapping the Electronic Criteria for the Formation of Persistent Metal-Coordinated Nitroxide Radicals journal July 2015
Light as a Catalytic Switch for Block Copolymer Architectures: Metal–Organic Insertion/Light Initiated Radical (MILRad) Polymerization journal September 2018
Photolysis of Pincer-Ligated PdII–Me Complexes in the Presence of Molecular Oxygen journal March 2017
Irradiation-Induced Palladium-Catalyzed Decarboxylative Heck Reaction of Aliphatic N-(Acyloxy)phthalimides at Room Temperature journal January 2018
Facile Quantum Yield Determination via NMR Actinometry journal March 2018
Cis -Selective Decarboxylative Alkenylation of Aliphatic Carboxylic Acids with Vinyl Arenes Enabled by Photoredox/Palladium/Uphill Triple Catalysis journal April 2018
Enantioselective α-Allylation of Anilines Enabled by a Combined Palladium and Photoredox Catalytic System journal March 2020
Dual Palladium/Photoredox-Catalyzed Enantioselective and Regioselective Decarboxylative Hydroaminoalkylation of Allenes journal March 2021
Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry journal November 2021
Regio- and Enantioselective Decarboxylative Allylic Benzylation Enabled by Dual Palladium/Photoredox Catalysis journal January 2022
An “On-Cycle” Precatalyst Enables Room-Temperature Polyfluoroarylation Using Sensitive Boronic Acids journal March 2018
Living Vinyl Addition Polymerization of Substituted Norbornenes by a t -Bu 3 P-Ligated Methylpalladium Complex journal February 2015
A Glove-Box- and Schlenk-Line-Free Protocol for Solid-State C–N Cross-Coupling Reactions Using Mechanochemistry journal October 2020
Femtosecond Absorption Spectroscopy of Transition Metal Charge-Transfer Complexes journal December 2003
Carbonylation Reactions of Alkyl Iodides through the Interplay of Carbon Radicals and Pd Catalysts journal April 2014
The Development of Versatile Methods for Palladium-Catalyzed Coupling Reactions of Aryl Electrophiles through the Use of P( t -Bu) 3 and PCy 3 as Ligands journal October 2008
Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis journal March 2013
Photochemistry of metal carbonyls journal August 1974
Shape of Multireference, Equation-of-Motion Coupled-Cluster, and Density Functional Theory Potential Energy Surfaces at a Conical Intersection journal June 2014
Organometallic photochemistry journal October 1983
Photophysical investigation of palladium(II) ortho-metalated complexes journal January 1989
Electronic Effects on Reductive Elimination To Form Carbon−Carbon and Carbon−Heteroatom Bonds from Palladium(II) Complexes journal March 2007
Redox Noninnocence of Nitrosoarene Ligands in Transition Metal Complexes journal June 2011
Luminescent Mononuclear and Binuclear Cyclometalated Palladium(II) Complexes of 6-Phenyl-2,2‘-bipyridines:  Spectroscopic and Structural Comparisons with Platinum(II) Analogues 1 , 2 journal January 2000
Trends of Metal-Carbon Bond Strengths in Transition Metal Complexes journal August 1995
Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions journal May 2000
Wavelength-dependent photosubstitution and excited-state dynamics of [Cr(CO)4(2,2'-bipyridine)]: a quantum yield and picosecond absorption study journal December 1992
Determination of the metal-hydrogen and metal-methyl bond dissociation energies of the second-row, Group 8 transition metal cations journal August 1984
Photochemistry of tris(2,2'-bipyridine)ruthenium(2+) ion (Ru(bpy)32+). Solvent effects journal August 1983
The Infrared Spectrum and Evidence for the Structure of a New Metal Carbonyl journal September 1962
Electronic structures of metal hexacarbonyls journal October 1968
Synthesis, Structure, and Reductive Elimination Chemistry of Three-Coordinate Arylpalladium Amido Complexes journal April 2004
Addition of Ammonia, Water, and Dihydrogen Across a Single Pd−Pd Bond journal August 2007
Stable Mononuclear Organometallic Pd(III) Complexes and Their C−C Bond Formation Reactivity journal June 2010
Room-Temperature C–H Arylation: Merger of Pd-Catalyzed C–H Functionalization and Visible-Light Photocatalysis journal November 2011
Reactivity and Stability of Dinuclear Pd(I) Complexes: Studies on the Active Catalytic Species, Insights into Precatalyst Activation and Deactivation, and Application in Highly Selective Cross-Coupling Reactions journal December 2011
Effect of Ligand Steric Properties and Halide Identity on the Mechanism for Oxidative Addition of Haloarenes to Trialkylphosphine Pd(0) Complexes journal May 2009
Photoinduced Radical Formation from the Complexes [Re(R)(CO)3(4,4‘-Me2-bpy)] (R = CH3, CD3, Et, iPr, Bz):  A Nanosecond Time-Resolved Emission, UV−Vis and IR Absorption, and FT-EPR Study journal October 1998
3 d-d Excited States of Ni(II) Complexes Relevant to Photoredox Catalysis: Spectroscopic Identification and Mechanistic Implications journal March 2020
Mechanistic Analysis of Metallaphotoredox C–N Coupling: Photocatalysis Initiates and Perpetuates Ni(I)/Ni(III) Coupling Activity journal August 2020
Aryl Amination Using Soluble Weak Base Enabled by a Water-Assisted Mechanism journal November 2020
Dual Polymerization Pathway for Polyolefin-Polar Block Copolymer Synthesis via MILRad: Mechanism and Scope journal December 2020
Excited-State Palladium-Catalyzed 1,2-Spin-Center Shift Enables Selective C-2 Reduction, Deuteration, and Iodination of Carbohydrates journal January 2021
Elucidating the Mechanism of Excited-State Bond Homolysis in Nickel–Bipyridine Photoredox Catalysts journal March 2022
Versatile Palladium-Catalyzed Approach to Acyl Fluorides and Carbonylations by Combining Visible Light- and Ligand-Driven Operations journal May 2022
Shining Visible Light on Reductive Elimination: Acridine–Pd-Catalyzed Cross-Coupling of Aryl Halides with Carboxylic Acids journal October 2022
Pd(0)/Blue Light Promoted Carboiodination Reaction – Evidence for Reversible C–I Bond Formation via a Radical Pathway journal October 2022
Photoinduced Formation of Hybrid Aryl Pd-Radical Species Capable of 1,5-HAT: Selective Catalytic Oxidation of Silyl Ethers into Silyl Enol Ethers journal May 2016
Tri(1-adamantyl)phosphine: Expanding the Boundary of Electron-Releasing Character Available to Organophosphorus Compounds journal May 2016
Photochemical Nickel-Catalyzed C–H Arylation: Synthetic Scope and Mechanistic Investigations journal September 2016
Understanding the Unusual Reduction Mechanism of Pd(II) to Pd(I): Uncovering Hidden Species and Implications in Catalytic Cross-Coupling Reactions journal March 2017
Visible-Light-Driven Carboxylation of Aryl Halides by the Combined Use of Palladium and Photoredox Catalysts journal July 2017
Irradiation-Induced Heck Reaction of Unactivated Alkyl Halides at Room Temperature journal November 2017
Long-Lived Charge-Transfer States of Nickel(II) Aryl Halide Complexes Facilitate Bimolecular Photoinduced Electron Transfer journal February 2018
Energy Transfer to Ni-Amine Complexes in Dual Catalytic, Light-Driven C–N Cross-Coupling Reactions journal November 2019
Transient Absorption Spectroscopy Offers Mechanistic Insights for an Iridium/Nickel-Catalyzed C–O Coupling journal February 2020
Kinetic and Computational Studies on Pd(I) Dimer-Mediated Halogen Exchange of Aryl Iodides journal October 2014
Thermodynamic Trends in Carbon−Hydrogen Bond Activation in Nitriles and Chloroalkanes at Rhodium journal August 2009
Spectroscopic and Excited-State Properties of Tri-9-anthrylborane I:  Solvent Polarity Effects journal July 2005
Different Mechanisms of Photochemical Re−Me and Re−Et Bond Homolysis in [Re(R)(CO)3(4,4‘-dimethyl-2,2‘-bipyridine)]. A Time-Resolved IR Spectroscopic Study Ranging from Picoseconds to Microseconds journal March 2006
Syntheses and Structures of Bulky Monophosphine-Ligated Methylpalladium Complexes:  Application to Homo- and Copolymerization of Norbornene and/or Methoxycarbonylnorbornene journal September 2006
Theoretical Study of Alternative Pathways for the Heck Reaction through Dipalladium and “Ligand-Free” Palladium Intermediates journal November 2008
Photochemistry of Cr(CO)4(bpy) (bpy = 2,2‘-Bipyridine) Studied by Time-Resolved Infrared Spectroscopy journal September 1996
Energetics of Homogeneous Intermolecular Vinyl and Allyl Carbon−Hydrogen Bond Activation by the 16-Electron Coordinatively Unsaturated Organometallic Fragment [Tp‘Rh(CNCH 2 CMe 3 )] journal January 1999
A highly active Ni(II)-triadamantylphosphine catalyst for ultrahigh-molecular-weight polyethylene synthesis journal January 2019
The merger of transition metal and photocatalysis journal July 2017
Structural variation in copper( i ) complexes with pyridylmethylamide ligands: structural analysis with a new four-coordinate geometry index, τ 4 journal January 2007
Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions—alternatives to PtBu3 journal January 2010
Visible light photoredox catalysis: applications in organic synthesis journal January 2011
Structural classification of metal complexes with three-coordinate centres journal January 2015
The photophysics of photoredox catalysis: a roadmap for catalyst design journal January 2016
Highly luminescent palladium( ii ) complexes with sub-millisecond blue to green phosphorescent excited states. Photocatalysis and highly efficient PSF-OLEDs journal January 2016
Solvent control of charge transfer excited state relaxation pathways in [Fe(2,2′-bipyridine)(CN) 4 ] 2− journal January 2018
Visible light-induced transition metal-catalyzed transformations: beyond conventional photosensitizers journal January 2017
Metal–organic insertion light initiated radical (MILRad) polymerization: photo-initiated radical polymerization of vinyl polar monomers with various palladium diimine catalysts journal January 2019
Tuning the interfacial and energetic interactions between a photoexcited conjugated polymer and open-shell small molecules journal January 2019
Photoexcited Pd(ii) auxiliaries enable light-induced control in C(sp3)–H bond functionalisation journal January 2020
Dalton communications. Synthesis and structural characterisation of [Pd4(µ3-CH)(µ-Cl)3(PBut3)4]: a tetrahedral palladium cluster with a µ3-methylidyne ligand journal January 1995
Synthesis and structural characterisation of [Pd 2 (µ-Br) 2 (PBu t 3 ) 2 ], an example of a palladium( I )–palladium( I ) dimer journal January 1996
Manipulating the properties of MLCT excited states journal January 2002
Cyclopalladated complexes of 4-aryl-2,1,3-benzothiadiazoles: new emitters in solution at room temperature journal January 2011
Dinuclear Pd(i) complexes—solely precatalysts? Demonstration of direct reactivity of a Pd(i) dimer with an aryl iodide journal January 2013
Photochemistry of the group VI hexacarbonyls in low temperature matrices. Part I. The pentacarbonyls of chromium, molybdenum, and tungsten journal January 1971
Irradiation-Induced Palladium-Catalyzed Direct C–H Alkylation of Heteroarenes with Tertiary and Secondary Alkyl Bromides journal April 2018
Tri-tert-butylphosphine [P(t-Bu)3]: An Electron-Rich Ligand for Palladium in Cross-Coupling Reactions journal January 2005
Luminescence from Transition‐Metal Complexes: Tris(2,2′‐bipyridine)‐ and Tris(1,10‐phenanthroline)Ruthenium(II) journal September 1965
Conical intersections and double excitations in time-dependent density functional theory journal March 2006
Photosensitized, energy transfer-mediated organometallic catalysis through electronically excited nickel(II) journal January 2017
Enantiodivergent Pd-catalyzed C–C bond formation enabled through ligand parameterization journal September 2018
A dual light-driven palladium catalyst: Breaking the barriers in carbonylation reactions journal April 2020
Asymmetric intermolecular allylic C–H amination of alkenes with aliphatic amines journal December 2022
Mechanistic Studies into Visible Light-Driven Carboxylation of Aryl Halides/Triflates by the Combined Use of Palladium and Photoredox Catalysts journal July 2021
Palladium(II) Complexes of 2,2,6,6-TetramethylpiperidineN-Oxyl Radical journal April 1977
Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Crosscoupling Reactions journal May 2020