4.6 Article

Rh(iii)-catalyzed [4+1] cyclization of aryl substituted pyrazoles with cyclopropanols via C-H activation

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, Organic

Rhodium(III)-Catalyzed Sequential Cyclization ofN-Boc Hydrazoneswith Propargylic Monofluoroalkynes via C-H Activation/C-FCleavage for the Synthesis of Spiro[cyclobutane-1,9?-indeno[1,2-a]indenes]

Cheng Deng et al.

Summary: An effective rhodium(III) catalysis was developed for the construction of valuable tetracyclic compounds. This method involved a domino process of C-H activation/[3 + 2] annulation/intramolecular Friedel-Crafts reaction using N-Bochydrazones and propargylic monofluoroalkynes as substrates, leading to the formation of fused tetracyclic spiro[cyclobutane-1,9'-indeno[1,2-a]indenes] with moderate to good yields and three C-C bond formations. Control experiments suggested that the C-H activation might be the rate-determining step.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Organic

Rh-Catalyzed [4+2] Annulation with a Removable Monodentate Structure toward Iminopyranes and Pyranones by C-H Annulation

Leiqing Fu et al.

Summary: The Rh-catalyzed reactions of N-pyridinyl enaminones with internal alkynes leading to the synthesis of iminopyranes via C-H bond activation and subsequent tautomeric O-H bond cleavage are reported. The pyridine ring in the amino group acts as an auxiliary monodentate site and can be easily removed by hydrolysis to afford pyranones.

ORGANIC LETTERS (2022)

Article Chemistry, Physical

Palladium-Catalyzed Carbothiolation of Alkenes and Alkynes for the Synthesis of Heterocycles

Tristan Delcaillau et al.

Summary: The intramolecular carbothiolation of unsaturated hydrocarbons using a palladium-NHC catalyst was reported. The reaction showed excellent tolerance and chemoselectivity, and could be applied to the synthesis of various sulfur-containing compounds.

ACS CATALYSIS (2022)

Article Chemistry, Applied

Three-Component Synthesis of Benzofuran-3(2H)-ones with Tetrasubstituted Carbon Stereocenters via Rh(III)-Catalyzed C-H/C-C Bond Activation and Cascade Annulation

Jinyuan Jiang et al.

Summary: A one-pot three-component synthesis of benzofuran-3(2H)-ones with tetrasubstituted carbon stereocenters has been successfully developed via Rh(III)-catalyzed C-H/C-C bond activation and cascade annulation, using salicylaldehydes, cyclopropanols, and alkyl alcohols as starting materials.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Article Chemistry, Organic

Weak Chelation-Assisted C4-Selective Alkylation of Indoles with Cyclopropanols via Sequential C-H/C-C Bond Activation

Tripti Paul et al.

Summary: A weak chelation-guided C4-alkylation of indoles catalyzed by Rh has been achieved using cyclopropanols as alkylating agents, involving cascade C-H and C-C bond activation. The practical features include a broad substrate scope, tolerance towards functional groups, and late-stage mutation of drug molecules.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Palladium-Catalyzed Domino Carbopalladation/Carbonylative Cyclization: Synthesis of Heterocycles bearing Oxindoles and 3-Acylbenzofuran/3-Acylindole Moieties

Ren-Rui Xu et al.

Summary: A novel and straightforward methodology for constructing bisheterocycles has been established. The protocol generates oxindole and 3-acylbenzofuran/3-acylindole moieties in a single one-step operation, with the formation of three C-C bonds and one C-O/C-N bond. A wide range of bisheterocycles bearing oxindoles and 3-acylbenzofurans/3-acylindoles were prepared in moderate to excellent yields with good functional group tolerance.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Rhodium-Catalyzed C2-Alkylation of Indoles with Cyclopropanols Using N,N-Dialkylcarbamoyl as a Traceless Directing Group

Kuppan Ramachandran et al.

Summary: An efficient rhodium-catalyzed method for the synthesis of C2-alkylated NH-free indoles has been achieved. This method offers several advantages, including the use of traceless directing group, good functional group tolerance, and broad applicability.

ORGANIC LETTERS (2022)

Review Chemistry, Multidisciplinary

Recent advances using cyclopropanols and cyclobutanols in ring-opening asymmetric synthesis

Hong Yan et al.

Summary: Due to high ring strain energies, cyclopropanols and cyclobutanols have a strong tendency of breaking the endocyclic C-C bonds to participate in versatile organic transformations. Ring-opening asymmetric synthesis of these compounds allows for the synthesis of linear or cyclic molecules with stereogenic centers.

GREEN SYNTHESIS AND CATALYSIS (2022)

Article Chemistry, Multidisciplinary

Hydrogen evolution-enabled rhodaelectro-catalyzed [4+2] annulations of purines and 7-deazapurines with alkynes

Chao Xu et al.

Summary: In this study, a rhodium-catalyzed electrochemical regioselective annulation of 6-phenylpurines and 6-phenyl-7-deazapurines with alkynes was successfully developed. This mild and green method enables a wide substrate scope and high functional group tolerance, providing a new series of polycyclic purinium and 7-deazapurinium salts in high yields.

CHEMICAL COMMUNICATIONS (2022)

Review Chemistry, Organic

Recent advances in the transition metal-free synthesis of heterocycles from α,β-unsaturated ketones

Kizhakkan Thiruthi Ashitha et al.

Summary: Heterocyclic compounds are widely used in various applications, and metal-free protocols are more advantageous while considering the toxicity of metal catalysts. Alpha,beta-unsaturated ketones serve as important building blocks in synthesis.

ORGANIC CHEMISTRY FRONTIERS (2022)

Review Chemistry, Organic

Recent advances in transition metal-catalyzed heteroannulative difunctionalization of alkenes via C-H activation for the synthesis of heterocycles

Jianchao Liu et al.

Summary: Heterocyclic compounds are fundamental structural motifs found in natural products, pharmaceuticals, and biologically active compounds. There is increasing interest in developing novel synthetic strategies for constructing these specific structural motifs. Alkenes, as sustainable, abundant, and versatile two-carbon synthons, have shown great potential for synthesizing heterocycles.

ORGANIC CHEMISTRY FRONTIERS (2022)

Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed Divergent C-H Functionalization of Five-Membered Heteroarenes

Siyeon Jeong et al.

Summary: The regiodivergent, non-directed C-H functionalization of five-membered heteroarenes with alkenes and alkynes has been successfully achieved, allowing systematic diversification of common structural cores. A carefully devised transition metal catalytic system and a judicious choice of metals, ligands, acid and base additives, and solvents are critical for achieving high selectivity in these reactions.

ACCOUNTS OF CHEMICAL RESEARCH (2021)

Article Chemistry, Organic

Cobalt(II)-Catalyzed C-H/N-H Functionalization and Annulation of N-(quinolin-8-yl)benzamide with Cyclopropanols

Jinkang Chen et al.

Summary: A new method for the synthesis of isoindolin-1-ones was developed through Co-catalyzed C-H/N-H functionalization and [4+1] annulation, showcasing its utility in late-stage modification of lithocholic acid derivatives and ibuprofen derivatives.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Rhodium(III)-Catalyzed Alkylation of 2-Arylquinazolin-4(3H)-ones with Cyclopropanols by Directing C-H Activation and Ring Opening at Ambient Temperature

Mu-Wang Chen et al.

Summary: An efficient method for the synthesis of beta-aryl ketones bearing the quinazolin-4(3H)-one scaffold was developed using Rh(III)-catalyzed C-H activation of arenes and C-C cleavage of cyclopropanols. This method has a wide substrate applicability and provides theoretical guidance for future research on quinazoline compounds.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Iron-Catalyzed Ring Opening of Cyclopropanols and Their 1,6-Conjugate Addition to p-Quinone Methides

Baliram B. Mane et al.

Summary: The novel iron-catalyzed ring opening of cyclopropanols and their 1,6-conjugate addition to p-quinone methides allows for the efficient synthesis of substituted phenols. This method features simple operation, mild reaction conditions, high yields, and a wide range of substrate applicability.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Enantioselective Conjugate Addition of Catalytically Generated Zinc Homoenolate

Yoshiya Sekiguchi et al.

Summary: An enantioselective conjugate addition reaction using a zinc homoenolate catalytically generated from cyclopropanol and added to an alpha,beta-unsaturated ketone was reported. The reaction produced highly substituted cyclopentene derivatives with good to high enantioselectivities through intramolecular aldol condensation of 1,6-diketones. The use of a chiral amino alcohol as a ligand-accelerated the catalysis of the homoenolate generation and its conjugate addition.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Review Chemistry, Multidisciplinary

Recent Advances in Theoretical Studies on Transition-Metal-Catalyzed Carbene Transformations

Xiaotian Qi et al.

Summary: Metal carbenes play a crucial role in modern organic synthesis, and computational studies of their transformation reactions with different nucleophiles can provide valuable mechanistic insights for the design of new reactions. Three generalized reaction models for carbene transformation with nucleophiles are proposed based on our computational results: intramolecular migratory insertion of metal carbene, intermolecular nucleophilic addition towards metal carbene, and outer-sphere nucleophilic addition to metal-ligated free carbene.

ACCOUNTS OF CHEMICAL RESEARCH (2021)

Article Chemistry, Organic

Rh(III)-Catalyzed [4+2] Cyclization of 2-Aryl-1H-benzo[d]imidazoles with Maleimides via C-H Activation

Chen Deng et al.

Summary: A novel rhodium-catalyzed cyclization reaction is described, allowing for the selective construction of a variety of functionalized compounds with high yields.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Ruthenium-catalyzed room-temperature coupling of α-keto sulfoxonium ylides and cyclopropanols for δ-diketone synthesis

Lili Fang et al.

Summary: A low-cost, room temperature ruthenium catalytic method was developed for the synthesis of delta-diketones by coupling alpha-keto sulfoxonium ylides with cyclopropanols. The mild protocol showed a broad substrate scope (47 examples) and high product yield (up to 99%), with mechanistic studies supporting a cyclopropanol ring opening, sulfoxonium ylide-derived carbenoid formation, migratory insertion C-C bond formation pathway.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Rh-Catalyzed cascade C-H activation/C-C cleavage/cyclization of carboxylic acids with cyclopropanols

Siqi Wang et al.

Summary: The novel Rh(iii)-catalyzed tandem process combining C-H activation, ring opening C-C cleavage, and cyclization of carboxylic acids with cyclopropanols allows for the synthesis of 3-substituted phthalides and alpha,beta-butenolides under mild conditions. This reaction shows excellent functional group tolerance and has been demonstrated to be useful for the rapid construction of bioactive compounds bearing a 3-substituted phthalide framework via late-stage functionalization.

CHEMICAL COMMUNICATIONS (2021)

Review Chemistry, Multidisciplinary

Transition-metal-catalyzed transformations of C-N single bonds: Advances in the last five years, challenges and prospects

Jun Liu et al.

Summary: This paper reviews recent research on the synthesis of 21 types of frequently-encountered molecules from simple N-containing compounds catalyzed by various transition metals, highlighting the importance of the formation and transformation of C-N bonds in organic synthetic chemistry.

GREEN SYNTHESIS AND CATALYSIS (2021)

Article Chemistry, Organic

Rhodium(iii)-catalyzed oxidative alkylation of N-aryl-7-azaindoles with cyclopropanols

Jidan Liu et al.

Summary: An efficient Rh(III)-catalyzed C-H oxidative alkylation of N-aryl-7-azaindoles with cyclopropanols by merging tandem C-H and C-C cleavage has been developed, featuring mild reaction conditions, high regioselectivity, and excellent functional group compatibility. The resulting beta-aryl ketone derivatives can be readily transformed into 7-azaindole-containing pi-extended polycyclic heteroarenes.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Helically Chiral Aromatics: The Synthesis of Helicenes by [2+2+2] Cycloisomerization of π-Electron Systems

Irena G. Stara et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

Article Chemistry, Organic

Selective Cross-Dehydrogenative C(sp3)-H Arylation with Arenes

Hong-Yan Hao et al.

ORGANIC LETTERS (2020)

Article Chemistry, Organic

Metal-Free Direct C-H beta-Carbonyl Alkylation of Heteroarenes with Cyclopropanols Mediated by K2S2O8

Liu Qiang et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Rhodium(III)-Catalyzed Asymmetric Borylative Cyclization of Cyclohexadienone-Containing 1,6-Dienes: An Experimental and DFT Study

Yun-Xuan Tan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Chemistry, Multidisciplinary

Rhodium-Catalyzed C(sp2)- or C(sp3)-H Bond Functionalization Assisted by Removable Directing Groups

Supriya Rej et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Organic

Recent advances in intramolecular C-O/C-N/C-S bond formation via C-H functionalization

Paran J. Borpatra et al.

ORGANIC CHEMISTRY FRONTIERS (2019)

Article Chemistry, Multidisciplinary

Electrooxidative Rhodium-Catalyzed C-H/C-H Activation: Electricity as Oxidant for Cross-Dehydrogenative Alkenylation

Youai Qiu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Divergent ring-opening coupling between cyclopropanols and alkynes under cobalt catalysis

Junfeng Yang et al.

CHEMICAL SCIENCE (2018)

Review Chemistry, Multidisciplinary

Chemistry and Properties of Indolocarbazoles

Tomasz Janosik et al.

CHEMICAL REVIEWS (2018)

Review Chemistry, Multidisciplinary

Electronic and Steric Tuning of a Prototypical Piano Stool Complex: Rh(III) Catalysis for C-H Functionalization

Tiffany Piou et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

Joshua R. Hummel et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Organic

Generation of benzosultams via a radical process with the insertion of sulfur dioxide

Kaida Zhou et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

Article Chemistry, Applied

Traceless Directing Group Assisted Cobalt-Catalyzed C-H Carbonylation of Benzylamines

Fei Ling et al.

ADVANCED SYNTHESIS & CATALYSIS (2017)

Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed C-H Alkylation Using Alkenes

Zhe Dong et al.

CHEMICAL REVIEWS (2017)

Review Chemistry, Multidisciplinary

Chiral Cyclopentadienyls: Enabling Ligands for Asymmetric Rh(III)-Catalyzed C-H Functionalizations

Baihua Ye et al.

ACCOUNTS OF CHEMICAL RESEARCH (2015)

Review Chemistry, Multidisciplinary

Synthesis of heterocycles via transition-metal-catalyzed hydroarylation of alkynes

Yoshihiko Yamamoto

CHEMICAL SOCIETY REVIEWS (2014)

Article Chemistry, Organic

Synthesis of 2,3-dihydro-1H-indazoles by Rh( III)-catalyzed C-H cleavage of arylhydrazines

Jinzhong Yao et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2014)

Review Chemistry, Multidisciplinary

Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions

Denise A. Colby et al.

ACCOUNTS OF CHEMICAL RESEARCH (2012)

Article Chemistry, Multidisciplinary

On the Interpretation of Deuterium Kinetic Isotope Effects in C?H Bond Functionalizations by Transition-Metal Complexes

Eric M. Simmons et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Review Chemistry, Multidisciplinary

C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation

Guoyong Song et al.

CHEMICAL SOCIETY REVIEWS (2012)

Review Chemistry, Multidisciplinary

Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation

Denise A. Colby et al.

CHEMICAL REVIEWS (2010)

Article Biochemistry & Molecular Biology

Synthesis and biological activities of isogranulatimide analogues

Bernadette Hugon et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2007)

Review Chemistry, Multidisciplinary

Isotope effects in C-H bond activation reactions by transition metals

WD Jones

ACCOUNTS OF CHEMICAL RESEARCH (2003)