Transition-Metal-Catalyzed Decarbonylative Coupling Reactions: Concepts, Classifications, and Applications

Nickel-Catalyzed C−S Bond Formation via Decarbonylative Thioetherification of Esters, Amides and Intramolecular Recombination Fragment Coupling of Thioesters

(2018) Shao-Chi Lee et al.   CHEMISTRY-A EUROPEAN JOURNAL

Ligand-Controlled Chemoselective C(acyl)–O Bond vs C(aryl)–C Bond Activation of Aromatic Esters in Nickel Catalyzed C(sp2)–C(sp3) Cross-Couplings

(2018) Adisak Chatupheeraphat et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Catalytic Ester to Stannane Functional Group Interconversion via Decarbonylative Cross-Coupling of Methyl Esters

(2018) Huifeng Yue et al.   ORGANIC LETTERS

Nickel-Mediated Decarbonylation of Simple Unstrained Ketones through the Cleavage of Carbon–Carbon Bonds

(2017) Toshifumi Morioka et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Decarbonylative Diaryl Ether Synthesis by Pd and Ni Catalysis

(2017) Ryosuke Takise et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Nickel-Catalyzed C–CN Bond Formation via Decarbonylative Cyanation of Esters, Amides, and Intramolecular Recombination Fragment Coupling of Acyl Cyanides

(2017) Adisak Chatupheeraphat et al.   ORGANIC LETTERS

Amide to Alkyne Interconversion via a Nickel/Copper-Catalyzed Deamidative Cross-Coupling of Aryl and Alkenyl Amides

(2017) Watchara Srimontree et al.   ORGANIC LETTERS

Decarbonylative Cyanation of Amides by Palladium Catalysis

(2017) Shicheng Shi et al.   ORGANIC LETTERS

Differentially Substituted Phosphines via Decarbonylation of Acylphosphines

(2017) Rongrong Yu et al.   ORGANIC LETTERS

Syntheses of Diverse Natural Products via Dual-Mode Lewis Acid Induced Cascade Cyclization Reactions

(2017) Chi-Sing Lee et al.   SYNLETT

Nickel-catalysed retro-hydroamidocarbonylation of aliphatic amides to olefins

(2017) Jiefeng Hu et al.   Nature Communications

Breaking Amides using Nickel Catalysis

(2017) Jacob E. Dander et al.   ACS Catalysis

Nickel-Catalyzed C–O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains

(2017) Xiangqian Liu et al.   ACS Catalysis

Synthesis of Biaryls through Nickel-Catalyzed Suzuki-Miyaura Coupling of Amides by Carbon-Nitrogen Bond Cleavage

(2016) Shicheng Shi et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Nickel-Catalyzed Decarbonylative Borylation of Amides: Evidence for Acyl C−N Bond Activation

(2016) Jiefeng Hu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Decarbonylative Silylation of Esters by Combined Nickel and Copper Catalysis for the Synthesis of Arylsilanes and Heteroarylsilanes

(2016) Lin Guo et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C−O Bond-Cleaving Alkylation: Prevention of Undesired β-Hydride Elimination

(2016) Xiangqian Liu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Nickel-Catalyzed Alkoxy-Alkyl Interconversion with Alkylborane Reagents through C−O Bond Activation of Aryl and Enol Ethers

(2016) Lin Guo et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Nickel-Catalyzed Activation of Acyl C−O Bonds of Methyl Esters

(2016) Liana Hie et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Functional Group Interconversion: Decarbonylative Borylation of Esters for the Synthesis of Organoboronates

(2016) Lin Guo et al.   CHEMISTRY-A EUROPEAN JOURNAL

N-Acylsaccharins as Amide-Based Arylating Reagents via Chemoselective N–C Cleavage: Pd-Catalyzed Decarbonylative Heck Reaction

(2016) Chengwei Liu et al.   JOURNAL OF ORGANIC CHEMISTRY

Palladium-Catalyzed Decarbonylative Cross-Coupling of Azinecarboxylates with Arylboronic Acids

(2016) Kei Muto et al.   ORGANIC LETTERS

Decarbonylative cross coupling of phthalimides with diorganozinc reagents—Efforts toward catalysis

(2016) Kimberly S. DeGlopper et al.   POLYHEDRON

Nickel-Catalyzed Decarbonylative Borylation and Silylation of Esters

(2016) Xinghui Pu et al.   ACS Catalysis

Nickel-Catalyzed Deamidative Step-Down Reduction of Amides to Aromatic Hydrocarbons

(2016) Aniruddha Dey et al.   ACS Catalysis

Nickel-Catalyzed Csp2–Csp3 Cross-Coupling via C–O Bond Activation

(2016) Lin Guo et al.   ACS Catalysis

The Retro-Hydroformylation Reaction

(2015) Shuhei Kusumoto et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective NC Activation

(2015) Guangrong Meng et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Ruthenium-catalyzed decarbonylative addition reaction of anhydrides with alkynes: a facile synthesis of isocoumarins and α-pyrones

(2015) Rashmi Prakash et al.   CHEMICAL COMMUNICATIONS

Nickel catalyzed dealkoxylative Csp2–Csp3 cross coupling reactions – stereospecific synthesis of allylsilanes from enol ethers

(2015) Lin Guo et al.   CHEMICAL COMMUNICATIONS

Ipso-Borylation of Aryl Ethers via Ni-Catalyzed C–OMe Cleavage

(2015) Cayetana Zarate et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Ni-Catalyzed Borylation of Aryl Fluorides via C–F Cleavage

(2015) Xiang-Wei Liu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Conversion of amides to esters by the nickel-catalysed activation of amide C–N bonds

(2015) Liana Hie et al.   NATURE

Rh-catalyzed C-C bond cleavage by transfer hydroformylation

(2015) S. K. Murphy et al.   SCIENCE

Rh-catalyzed decarbonylation of conjugated ynones via carbon–alkyne bond activation: reaction scope and mechanistic exploration via DFT calculations

(2015) Alpay Dermenci et al.   Chemical Science

Decarbonylative organoboron cross-coupling of esters by nickel catalysis

(2015) Kei Muto et al.   Nature Communications

Metal catalyzed cross-coupling of aryl and benzyl methyl sulfides: nickel catalyzed Caryl–Csp3 and Csp3–Csp3 bond formations

(2015) Matthias Leiendecker et al.   Organic Chemistry Frontiers

Metal-Catalyzed Dealkoxylative CarylC sp 3 Cross-Coupling-Replacement of Aromatic Methoxy Groups of Aryl Ethers by Employing a Functionalized Nucleophile

(2014) Matthias Leiendecker et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Nickel-Catalyzed Reductive and Borylative Cleavage of Aromatic Carbon–Nitrogen Bonds in N-Aryl Amides and Carbamates

(2014) Mamoru Tobisu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes

(2013) Alpay Dermenci et al.   ORGANIC LETTERS

Decarbonylative C-C bond forming reactions mediated by transition metals

(2013) Alpay Dermenci et al.   Science China-Chemistry

Extrusion of CO from Aryl Ketones: Rhodium(I)-Catalyzed CC Bond Cleavage Directed by a Pyridine Group

(2012) Zhi-Quan Lei et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Decarbonylative C–H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A

(2012) Kazuma Amaike et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Rhodium-Catalyzed Cross-Coupling Reactions of Carboxylate and Organoboron Compounds via Chelation-Assisted C–C Bond Activation

(2012) Jingjing Wang et al.   ORGANOMETALLICS

Carboxylates as sources of carbon nucleophiles and electrophiles: comparison of decarboxylative and decarbonylative pathways

(2012) Wojciech I. Dzik et al.   Chemical Science

Magical Power of Transition Metals: Past, Present, and Future (Nobel Lecture)

(2011) Ei-ichi Negishi   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Large-Scale Applications of Transition Metal-Catalyzed Couplings for the Synthesis of Pharmaceuticals

(2011) Javier Magano et al.   CHEMICAL REVIEWS

Palladium-catalyzed carbonylative coupling reactions between Ar–X and carbon nucleophiles

(2011) Xiao-Feng Wu et al.   CHEMICAL SOCIETY REVIEWS

Decarboxylative coupling reactions: a modern strategy for C–C-bond formation

(2011) Nuria Rodríguez et al.   CHEMICAL SOCIETY REVIEWS

Nickel-Mediated Decarbonylative Cross-Coupling of Phthalimides with in Situ Generated Diorganozinc Reagents

(2011) Sarah E. Havlik et al.   JOURNAL OF ORGANIC CHEMISTRY

Rhodium-Catalyzed Oxidative C−H Arylation of 2-Arylpyridine Derivatives via Decarbonylation of Aromatic Aldehydes

(2010) Qi Shuai et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Decarbonylative Cycloaddition of Phthalimides with 1,3-Dienes

(2010) Kyohei Fujiwara et al.   ORGANIC LETTERS

Rhodium-Catalyzed Direct Alkenylation and Arylation of Arene C−H Bonds via Decarbonylation of Cinnamoyl Chlorides, Cinnamic Anhydrides, and Poly(aroyl) Chlorides

(2010) Wenjing Ye et al.   ORGANOMETALLICS

Efficient Rh(I)-Catalyzed Direct Arylation and Alkenylation of Arene C−H Bonds via Decarbonylation of Benzoic and Cinnamic Anhydrides

(2009) Weiwei Jin et al.   ORGANIC LETTERS

Nickel-Catalyzed Decarbonylative Addition of Anhydrides to Alkynes

(2008) Yuichi Kajita et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Nickel-Catalyzed Decarbonylative Addition of Phthalimides to Alkynes

(2008) Yuichi Kajita et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Rhodium-Catalyzed Regioselective C−H Functionalization via Decarbonylation of Acid Chlorides and C−H Bond Activation under Phosphine-Free Conditions

(2008) Xiaodan Zhao et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY