4.5 Review

Recent Development in the Catalytic Applications of Pd-NHC (NHC=N-Heterocyclic Carbene) Compounds in Amide C-N Activation Reactions

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Multidisciplinary

Mechanochemical Solvent-Free Suzuki-Miyaura Cross-Coupling of Amides via Highly Chemoselective N-C Cleavage

Jin Zhang et al.

Summary: A highly chemoselective, solvent-free mechanochemical strategy for the cross-coupling of amides by N-C bond activation has been reported. The method shows excellent selectivity, functional group tolerance, and can be applied for late-stage functionalization of complex molecules. This extends the repertoire of N-C bond interconversions to solid-state environmentally friendly mechanochemical methods.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Physical

Palladium-NHC (NHC = N-heterocyclic Carbene)-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkyl Amides

Chang-An Wang et al.

Summary: We report the Pd-catalyzed Suzuki-Miyaura cross-coupling of aliphatic amides. The selective N-C(O) cleavage to form C-C bonds from aliphatic amides has been a major challenge in Pd catalysis. This study addresses this longstanding problem by using N,N-pym/Boc amides as reagents for cross-coupling and steric tuning of Pd(II)-NHC catalysts. The method is effective for various degrees of aliphatic amide derivatives and the catalyst system is user-friendly. Mechanistic studies support the twist of amide bond and external n(N) -> pi(C=O/Ar)* delocalization as a unified enabling feature of N,N-pym/Boc amides in selective N-C(O) bond activation. This method provides a rare example of Pd-NHC-catalyzed cross-coupling of aliphatic acyl amide electrophiles.

ACS CATALYSIS (2022)

Article Chemistry, Multidisciplinary

A novel electromagnetic mill promoted mechanochemical solid-state Suzuki-Miyaura cross-coupling reaction using ultra-low catalyst loading

Xin Li et al.

Summary: This article reports on a solid-state Suzuki-Miyaura cross-coupling reaction promoted by electromagnetic milling with ultra-low palladium loading. The method demonstrates a wide substrate scope, good functional group tolerance, efficient gram-scale synthesis, and relatively high yields. The utility of this strategy is exemplified in the modification of photoluminescent molecules, cross-coupling of slightly soluble compounds, and synthesis of bioactive molecules.

GREEN CHEMISTRY (2022)

Review Chemistry, Multidisciplinary

BIAN-NHC Ligands in Transition-Metal-Catalysis: A Perfect Union of Sterically Encumbered, Electronically Tunable N-Heterocyclic Carbenes?

Changpeng Chen et al.

Summary: The discovery of NHCs as ancillary ligands has greatly improved catalytic processes, with BIAN-NHC ligands in particular showing enhanced reactivity due to combinations of electronic and steric properties. The development of BIAN-NHC ligands has led to major advancements in catalysis and offers a practical alternative to classical NHCs.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Organic

[(NHC)PdCl2(Aniline)] Complexes: Easily Synthesized, Highly Active Pd(II)-NHC Precatalysts for Cross-Coupling Reactions

Qinqin Xia et al.

Summary: This study reports the synthesis, characterization, and reactivity of [(NHC)PdCl2(aniline)] complexes, which are highly active catalysts in various Suzuki-Miyaura reactions. The introduction of broadly available anilines as stabilizing ligands for well-defined Pd(II)-NHC catalysts has significant potential in fine-tuning challenging cross-coupling reactions. The commercialization of the parent catalyst [Pd(IPr)(AN)Cl-2] offers broad access for reaction screening and optimization.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Green-Solvent Selection for Acyl Buchwald-Hartwig Cross-Coupling of Amides (Transamidation)

Peng Lei et al.

Summary: Solvent selection is crucial in chemical processes, and this study evaluated green solvents for acyl Buchwald-Hartwig cross-coupling, providing the first green-solvent selection guide for this process. Results identified MTBE and 2-MeTHF as preferred alternative solvents with superior properties.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2021)

Article Chemistry, Organic

Evaluation of Cyclic Amides as Activating Groups in N-C Bond Cross-Coupling: Discovery of N-Acyl-δ-valerolactams as Effective Twisted Amide Precursors for Cross-Coupling Reactions

Md Mahbubur Rahman et al.

Summary: The study compares a series of cyclic amides as activating groups in amide N-C(O) bond cross-coupling, and finds that N-acyl-delta-valerolactams are a highly effective class of mono-N-acyl-activated amide precursors.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Applied

Suzuki-Miyaura Cross-Coupling of Amides using Well-Defined, Air-Stable [(PR3)2Pd(II)X2] Precatalysts

Siyue Ma et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Article Chemistry, Multidisciplinary

Robust NHC-palladacycles-catalyzed Suzuki-Miyaura cross-coupling of amides via C-N activation

Qinyue Deng et al.

GREEN SYNTHESIS AND CATALYSIS (2020)

Review Chemistry, Multidisciplinary

N-Boc-Amides in Cross-Coupling Reactions

Yann Bourne-Branchu et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Review Chemistry, Multidisciplinary

Recent Advances in the Metal-Catalyzed Activation of Amide Bonds

Moreshwar B. Chaudhari et al.

CHEMISTRY-AN ASIAN JOURNAL (2019)

Review Biochemistry & Molecular Biology

Well-Defined Pre-Catalysts in Amide and Ester Bond Activation

Sandeep R. Vemula et al.

MOLECULES (2019)

Review Chemistry, Multidisciplinary

Electronic Properties of N-Heterocyclic Carbenes and Their Experimental Determination

Han Vinh Huynh

CHEMICAL REVIEWS (2018)

Article Chemistry, Multidisciplinary

Reversible Twisting of Primary Amides via Ground State N-C(O) Destabilization: Highly Twisted Rotationally Inverted Acyclic Amides

Guangrong Meng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Organic

Palladium-Catalyzed Carbonylative Coupling Reactions of N,N-Bis(methanesulfonyl)amides through C-N Bond Cleavage

Minkyung Lim et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Inorganic & Nuclear

N-heterocyclic carbene palladium(II)-catalyzed Suzuki-Miyaura cross coupling of N-acylsuccinimides by C-N cleavage

Tao Wang et al.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2018)

Article Chemistry, Organic

Pd-PEPPSI: Pd-NHC Precatalyst for Suzuki-Miyaura Cross-Coupling Reactions of Amides

Peng Lei et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Pd(NHC)-catalyzed alkylsulfonylation of boronic acids: a general and efficient approach for sulfone synthesis

Haibo Zhu et al.

CHEMICAL COMMUNICATIONS (2017)

Review Chemistry, Multidisciplinary

Cross-coupling of aromatic esters and amides

Ryosuke Takise et al.

CHEMICAL SOCIETY REVIEWS (2017)

Article Chemistry, Multidisciplinary

Quantifying and understanding the steric properties of N-heterocyclic carbenes

Adrian Gomez-Suarez et al.

CHEMICAL COMMUNICATIONS (2017)

Article Chemistry, Multidisciplinary

Structural Characterization of N-Alkylated Twisted Amides: Consequences for Amide Bond Resonance and N-C Cleavage

Feng Hu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Palladium-catalyzed Sonogashira coupling of amides: access to ynones via C-N bond cleavage

Ming Cui et al.

CHEMICAL COMMUNICATIONS (2016)

Article Chemistry, Multidisciplinary

Total Synthesis and Characterization of 7-Hypoquinuclidonium Tetrafluoroborate and 7-Hypoquinuclidone BF3 Complex

Marc Liniger et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Organic

Cross-Coupling of Amides by N-C Bond Activation

Guangrong Meng et al.

SYNLETT (2016)

Article Chemistry, Physical

Nickel-Catalyzed Alkylation of Amide Derivatives

Bryan J. Simmons et al.

ACS CATALYSIS (2016)

Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed Direct Addition of Unactivated C-H Bonds to Polar Unsaturated Bonds

Lei Yang et al.

CHEMICAL REVIEWS (2015)

Article Chemistry, Multidisciplinary

Towards a holistic approach to metrics for the 21st century pharmaceutical industry

C. Robert McElroy et al.

GREEN CHEMISTRY (2015)

Article Chemistry, Inorganic & Nuclear

Palladium-catalyzed acylative cross-coupling of amides with diarylborinic acids and sodium tetraarylborates

Xijing Li et al.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

The Most Reactive Amide As a Transition-State Mimic For cis-trans Interconversion

Igor V. Komarov et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Review Chemistry, Multidisciplinary

Selection of boron reagents for Suzuki-Miyaura coupling

Alastair J. J. Lennox et al.

CHEMICAL SOCIETY REVIEWS (2014)

Review Biotechnology & Applied Microbiology

Integrated furfural production as a renewable fuel and chemical platform from lignocellulosic biomass

Charles M. Cai et al.

JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY (2014)

Article Chemistry, Multidisciplinary

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

Mamoru Tobisu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Review Multidisciplinary Sciences

An overview of N-heterocyclic carbenes

Matthew N. Hopkinson et al.

NATURE (2014)

Review Chemistry, Applied

Carbon-Heteroatom Coupling Using Pd-PEPPSI Complexes

Cory Valente et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2014)

Review Green & Sustainable Science & Technology

Production, properties and catalytic hydrogenation of furfural to fuel additives and value-added chemicals

Kai Yan et al.

RENEWABLE & SUSTAINABLE ENERGY REVIEWS (2014)

Article Chemistry, Organic

Acenaphthoimidazolium chloride-enabled nickel-catalyzed amination of bulky aryl tosylates

Jian Jiang et al.

ORGANIC CHEMISTRY FRONTIERS (2014)

Review Chemistry, Multidisciplinary

Chemistry of Bridged Lactams and Related Heterocycles

Michal Szostak et al.

CHEMICAL REVIEWS (2013)

Review Chemistry, Multidisciplinary

The Development of Bulky Palladium NHC Complexes for the Most-Challenging Cross-Coupling Reactions

Cory Valente et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Article Chemistry, Multidisciplinary

Suzuki reactions of extended scope: the '9-MeO-9-BBN variant' as a complementary format for cross-coupling

Guenter Seidel et al.

CHEMICAL COMMUNICATIONS (2012)

Article Chemistry, Inorganic & Nuclear

New catalysts with unsymmetrical N-heterocyclic carbene ligands

Johanna Tornatzky et al.

DALTON TRANSACTIONS (2012)

Article Chemistry, Inorganic & Nuclear

[Pd(IPr*)(3-Cl-pyridinyl)Cl2]: A Novel and Efficient PEPPSI Precatalyst

Anthony Chartoire et al.

ORGANOMETALLICS (2012)

Review Chemistry, Multidisciplinary

N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union

George C. Fortman et al.

CHEMICAL SOCIETY REVIEWS (2011)

Review Chemistry, Multidisciplinary

Activation of Inert Alkenyl/Aryl C-O Bond and Its Application in Cross-Coupling Reactions

Bi-Jie Li et al.

CHEMISTRY-A EUROPEAN JOURNAL (2011)

Article Chemistry, Medicinal

The Medicinal Chemist's Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates

Stephen D. Roughley et al.

JOURNAL OF MEDICINAL CHEMISTRY (2011)

Review Multidisciplinary Sciences

Rethinking amide bond synthesis

Vijaya R. Pattabiraman et al.

NATURE (2011)

Review Chemistry, Multidisciplinary

Cross-Dehydrogenative Coupling (CDC): Exploring C-C Bond Formations beyond Functional Group Transformations

Chao-Jun Li

ACCOUNTS OF CHEMICAL RESEARCH (2009)

Review Chemistry, Multidisciplinary

Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality

Xiao Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Review Chemistry, Multidisciplinary

Well-Defined N-Heterocyclic Carbenes-Palladium(II) Precatalysts for Cross-Coupling Reactions

Nicolas Marion et al.

ACCOUNTS OF CHEMICAL RESEARCH (2008)

Review Chemistry, Multidisciplinary

Metal-organic cooperative catalysis in C-H and C-C bond activation and its concurrent recovery

Young Jun Park et al.

ACCOUNTS OF CHEMICAL RESEARCH (2008)

Article Chemistry, Organic

One-pot amidation of olefins through Pd-catalyzed coupling of alkylboranes and carbamoyl Chlorides

Yoshizumi Yasui et al.

JOURNAL OF ORGANIC CHEMISTRY (2007)

Review Chemistry, Multidisciplinary

Aryl-aryl bond formation by transition-metal-catalyzed direct arylation

Dino Alberico et al.

CHEMICAL REVIEWS (2007)

Review Chemistry, Multidisciplinary

Palladium complexes of N-heterocyclic carbenes as catalysts for cross-coupling reactions - A synthetic chemist's perspective

Eric Assen B. Kantchev et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

Article Multidisciplinary Sciences

Synthesis and structural analysis of 2-quinuclidonium tetrafluoroborate

Kousuke Tani et al.

NATURE (2006)

Review Multidisciplinary Sciences

C-H bond functionalization in complex organic synthesis

K Godula et al.

SCIENCE (2006)

Article Chemistry, Multidisciplinary

Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions

N Marion et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Review Chemistry, Multidisciplinary

Monoligated palladium species as catalysts in cross-coupling reactions

U Christmann et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

Article Chemistry, Inorganic & Nuclear

Synthetic and structural studies of (NHC)Pd(allyl)Cl complexes (NHC = N-heterocyclic carbene)

MS Viciu et al.

ORGANOMETALLICS (2004)

Review Chemistry, Multidisciplinary

Transition metal-catalyzed carbon-carbon bond activation

CH Jun

CHEMICAL SOCIETY REVIEWS (2004)

Review Chemistry, Applied

Catalytic methods for C-H bond functionalization: Application in organic synthesis

F Kakiuchi et al.

ADVANCED SYNTHESIS & CATALYSIS (2003)

Review Chemistry, Multidisciplinary

Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion

HML Davies et al.

CHEMICAL REVIEWS (2003)

Article Chemistry, Organic

Synthesis, structure and reactions of the most twisted amide

AJ Kirby et al.

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 (2001)