4.4 Review

Recent Progress in Transition Metal Catalyzed C(sp3)-H Nitrene Insertion Reactions Assisted by Directing Groups

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

Copper-Mediated and Catalyzed C-H Bond Amination via Chelation Assistance: Scope, Mechanism and Synthetic Applications

Jiao-Li Ma et al.

Summary: This article summarizes the recent research progress in copper-catalyzed C-H amination and briefly describes the mechanisms of representative reactions, providing insights for the development of highly practical and more environmentally friendly processes.

CHINESE JOURNAL OF CHEMISTRY (2022)

Article Chemistry, Organic

Recent advances and prospects in the cobalt-catalyzed amination reactions

Padinjare Veetil Saranya et al.

Summary: This review summarizes the crucial role of the amino group in the production of molecules with interesting biological activity in the pharmaceutical industry, and discusses the applications of cobalt catalysts in amination reactions.

TETRAHEDRON (2022)

Review Chemistry, Multidisciplinary

Construction of C-N bonds from small-molecule precursors through heterogeneous electrocatalysis

Junnan Li et al.

Summary: Energy-intensive thermochemical processes in chemical manufacturing contribute significantly to global CO2 emissions. To achieve sustainability, scientists are developing renewable energy-powered electrochemical technologies as alternatives. This review focuses on the emerging area of heterogeneous electrocatalysis for C-N bond formation.

NATURE REVIEWS CHEMISTRY (2022)

Review Chemistry, Multidisciplinary

Transition Metal-Catalyzed Regioselective Direct C-H Amidation: Interplay between Inner- and Outer-Sphere Pathways for Nitrene Cross-Coupling Reactions

Bingnan Du et al.

Summary: Summary: This Account summarizes the development of C-N bond cross-coupling reactions via C-H activation. Regioselective protocols targeting C(sp(3))-H and C(aryl)-H bonds have been successfully developed by exploiting inner-sphere and outer-sphere reaction pathways. The mechanistic underpinning of the selectivity of different C-H bonds and related studies on the affiliated catalytic systems are discussed.

ACCOUNTS OF CHEMICAL RESEARCH (2022)

Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Enantioselective Synthesis of β-Amino Alcohols via Desymmetrization of gem-Dimethyl Groups

Bingxian Liu et al.

Summary: Desymmetrization of gem-dimethyl groups en route to the rhodium(III)-catalyzed enantioselective sp(3) C-H amidation leads to the synthesis of synthetically important beta-amino alcohol derivatives in moderate to good yields and high enantioselectivity. The high enantioselectivity is achieved through the use of an appropriate oxime directing group, sterically biased gem-groups in the C-H substrate, and the high reactivity of the amidating reagent.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Physical

Ni-Catalyzed Intermolecular C(sp3)-H Amidation Tuned by Bidentate Directing Groups

Yeong Bum Kim et al.

Summary: This study revealed a nickel-catalyzed intermolecular C(sp(3))-H amidation using organic azides as nitrene precursors. Enhanced amidation efficiency was achieved by introducing an electronically tailored directing group. Experimental and computational studies indicated that a putative nickel(III)-nitrenoid species serves as a key intermediate in the C-N bond-forming process.

ACS CATALYSIS (2021)

Article Chemistry, Physical

Development of Pseudo-C2-symmetric Chiral Binaphthyl Monocarboxylic Acids for Enantioselective C(sp3)-H Functionalization Reactions under Rh(III) Catalysis

Yoshimi Kato et al.

Summary: By introducing pseudo-C2 symmetric tunable chiral carboxylic acids, the study achieved enantioselective C(sp(3))-H amidation reactions of substrates such as 2-alkylpyridines, improving the chiral selectivity towards the substrates.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Thioether-Directed NiH-Catalyzed Remote γ-C(sp3)-H Hydroamidation of Alkenes by 1,4,2-Dioxazol-5-ones

Bingnan Du et al.

Summary: A NiH-catalyzed thioether-directed cyclometalation strategy allows for remote methylene C-H bond amidation of unactivated alkenes. This strategy shows high yields and remarkable regioselectivity in the preparation of amide products.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Physical

Iridium(III)-Catalyzed Direct Intermolecular Chemoselective α-Amidation of Masked Aliphatic Carboxylic Acids with Dioxazolones via Nitrene Transfer

Sanjit K. Mahato et al.

Summary: The Ir(III)-catalyzed direct alpha-C-H amidation of imidazole-masked aliphatic carboxylic acids with dioxazolones was successfully achieved, with the key role of the imidazole moiety as a directing group. The products can be easily converted to esters and amides, and the reaction demonstrated a broad substrate scope. Investigating the reaction mechanism led to the proposal of an iridium nitrene intermediate.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

A New Dioxazolone for the Synthesis of 1,2-Aminoalcohols via Iridium(III)-Catalyzed C(sp3)-H Amidation

Kevin Antien et al.

Summary: We developed a new reagent that exhibits high reactivity in the oxime-directed iridium(III)-catalyzed amidation reaction, resulting in amide products that can be easily hydrolyzed. This method is compatible with both primary C-H bonds of alcohols and secondary C-H bonds of cyclic secondary alcohols, providing a mild and general reaction.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Review Chemistry, Multidisciplinary

Dirhodium tetracarboxylates as catalysts for selective intermolecular C-H functionalization

Huw M. L. Davies et al.

NATURE REVIEWS CHEMISTRY (2019)

Article Chemistry, Inorganic & Nuclear

Chiral 2-Aryl Ferrocene Carboxylic Acids for the Catalytic Asymmetric C(sp3)-H Activation of Thioamides

Daichi Sekine et al.

ORGANOMETALLICS (2019)

Article Chemistry, Multidisciplinary

Catalytic Enantioselective Methylene C(sp3)-H Amidation of 8-Alkylquinolines Using a Cp*RhIII/Chiral Carboxylic Acid System

Seiya Fukagawa et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Enantioselective C(sp3)-H Amidation of Thioamides Catalyzed by a CobaltIII/Chiral Carboxylic Acid Hybrid System

Seiya Fukagawa et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Site- selective C( sp3)- H amination of thioamide with anthranils under Cp* CoIII catalysis

Rui-Hua Liu et al.

CHEMICAL COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

Dithiane-directed Rh(III)-catalyzed amidation of unactivated C(sp3)-H bonds

Heyao Shi et al.

CHEMICAL SCIENCE (2019)

Article Chemistry, Multidisciplinary

Thioamide-Directed Cobalt(III)-Catalyzed Selective Amidation of C(sp3)-H Bonds

Peng Wen Tan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Iridium(III)-Catalyzed Regioselective Intermolecular Unactivated Secondary Csp3-H Bond Amidation

Xinsheng Xiao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Anthranil: An Aminating Reagent Leading to Bifunctionality for Both C(sp3)-H and C(sp2)-H under Rhodium(III) Catalysis

Songjie Yu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Rh-Catalyzed Direct Amination of Unactivated C(sp3)-H bond with Anthranils Under Mild Conditions

Conghui Tang et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Article Chemistry, Multidisciplinary

Cp*CoIII-Catalyzed C(sp3)-H Bond Amidation of 8-Methylquinoline

Nagaraju Barsu et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Article Chemistry, Multidisciplinary

Rhodium(III)-Catalyzed Activation of Csp3-H Bonds and Subsequent Intermolecular Amidation at Room Temperature

Xiaolei Huang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Rhodium(III)-Catalyzed Amidation of Unactivated C(sp3)H Bonds

He Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Site-Selective Alkylation of Unactivated C(sp3)-H Bonds

Xuesong Wu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Direct Arylation of C(sp3)-H Bonds in Aliphatic Amides via Bidentate-Chelation Assistance

Yoshinori Aihara et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Iridium-Catalyzed Intermolecular Amidation of sp3 C-H Bonds: Late-Stage Functionalization of an Unactivated Methyl Group

Taek Kang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Palladium(0)-Catalyzed Alkynylation of C(sp3)-H Bonds

Jian He et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Picolinamide-Directed Alkylation of Unactivated C(sp3)-H Bonds with Alkyl Iodides

Shu-Yu Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Chemistry, Multidisciplinary

Palladium-catalyzed N-(2-pyridyl)sulfonyl-directed C(sp(3))-H gamma-arylation of amino acid derivatives

Nuria Rodriguez et al.

CHEMICAL SCIENCE (2013)

Article Chemistry, Organic

Recent advances in transition metal-catalyzed N-atom transfer reactions of azides

Tom G. Driver

ORGANIC & BIOMOLECULAR CHEMISTRY (2010)

Review Multidisciplinary Sciences

Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion

Huw M. L. Davies et al.

NATURE (2008)

Article Chemistry, Multidisciplinary

Intermolecular amidation of unactivated sp2 and sp3 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion

Hung-Yat Thu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Review Multidisciplinary Sciences

C-H bond functionalization in complex organic synthesis

K Godula et al.

SCIENCE (2006)