ArticleAccounts of chemical research2022
Mechanism-Driven Development of Group 10 Metal-Catalyzed Decarbonylative Coupling Reactions.
Article in Accounts of chemical research, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 12 papers.
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12 citing papers in PubMed.
- Pd-Catalyzed Arylative Lossen Rearrangement: Synthesis of Secondary Amines from Aryl/Alkyl Carboxylic Acids and Aryl Halides.Journal of the American Chemical Society · 2026Article
- Stereoretentive decarbonylative C(spNature · 2026Article
- Palladium-Catalyzed Decarbonylative C-H Difluoromethylation of Azoles.Organic letters · 2025Article
- The Divergent Reactivity of Acid Chlorides Under Transition Metal Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Review
- A decarbonylative approach to alkylnickel intermediates and C(spScience (New York, N.Y.) · 2024Article
- Divergent Transformations of Aromatic Esters: Decarbonylative Coupling, Ester Dance, Aryl Exchange, and Deoxygenative Coupling.Accounts of chemical research · 2024Article
- Ligand Relay for Nickel-Catalyzed Decarbonylative Alkylation of Aroyl Chlorides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Article
- Rational design of super reductive EDA photocatalyst for challenging reactions: a theoretical and experimental study.RSC advances · 2024Article
- Palladium-Catalyzed Decarbonylative Coupling of (Hetero)Aryl Boronate Esters with Difluorobenzyl Glutarimides.Organic letters · 2023Article
- Distinguishing Competing Mechanistic Manifolds for C(acyl)-N Functionalization by a Ni/JACS Au · 2023Article
- Merging the Norrish type I reaction and transition metal catalysis: photo- and Rh-promoted borylation of C-C σ-bonds of aryl ketones.Chemical science · 2023Article
Corrections and comments
- Erratum issued
Authors and funding
3 authors.
Funding
Abstract
Transition-metal-catalyzed cross-coupling reactions are widely used in both academia and industry for the construction of carbon-carbon and carbon-heteroatom bonds. The vast majority of cross-coupling reactions utilize aryl (pseudo)halides as the electrophilic coupling partner. Carboxylic acid derivatives (RC(O)X) represent a complementary class of electrophiles that can engage in decarbonylative couplings to produce analogous products. This decarbonylative approach offers the advantage that RC(O)X are abundant and inexpensive. In addition, decarbonylative coupling enables both intramolecular (between R and X of the carboxylic acid derivative) as well as intermolecular bond-forming reactions (in which an exogeneous nucleophile is coupled with the R group derived from RC(O)X). In these intermolecular reactions, the X-substituent on the carboxylic acid can be tuned to facilitate both oxidative addition and transmetalation, thus eliminating the need for an exogeneous base. This Account details our group's development of a diverse variety of base-free decarbonylative coupling reactions catalyzed by group 10 metals. Furthermore, it highlights how catalyst design can be guided by stoichiometric organometallic studies of these systems.Our early studies focused on
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