☆ 4.6 Article

Rh(iii)-catalyzed (5+2)-cycloaddition reactions of ortho-hydroxyethyl phenols with internal alkynes: efficient synthesis of benzoxepines

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

Related references

Note: Only part of the references are listed.

Article Chemistry, Organic

Enantioselective Friedel-Crafts Alkylation of Furans with o-Quinone Methide Using a Chiral Oxazaborolidinium Ion Catalyst

Yoon Sung Cho et al.

Summary: A chiral Lewis acid-catalyzed enantioselective Friedel-Crafts alkylation using in situ-generated o-quinone methides has been developed. The reaction showed high yield (up to 99%) and excellent enantioselectivity (up to >99% ee) in the presence of a chiral oxazaborolidinium ion catalyst.

ORGANIC LETTERS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Electrooxidative palladium- and enantioselective rhodium-catalyzed [3+2] spiroannulations

Wen Wei et al.

Summary: This study demonstrates the synthesis of biologically relevant three-dimensional spirocyclic compounds through electrocatalysis, using palladium and rhodium(iii) catalysts, with electricity as a green oxidant. The spiroannulation reactions were successfully achieved with a wide substrate scope under mild conditions in an undivided cell setup, with molecular hydrogen as the sole byproduct.

CHEMICAL SCIENCE (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Scalable Rhodaelectro-Catalyzed Expedient Access to Seven-Membered Azepino[3,2,1-hi]indoles via [5

Yumeng Yuan et al.

Summary: In this study, a rhodaelectrocatalyzed reaction was established to synthesize seven-membered azepino[3,2,1-hi]indoles using alkynes and 7-arylindoles as substrates, with electricity as the sole oxidant. The reaction was successfully scaled up to gram-scale by flow-electrocatalysis. Two key intermediates, rhodium(III) species, were isolated and fully characterized. Cyclovoltammetric analysis, X-ray photoelectron spectroscopy studies, and density functional theory calculations suggested the presence of a rhodium(III-IV-II-III) manifold.

CCS CHEMISTRY (2022)

Add to Collection

Article Chemistry, Organic

Total Synthesis of Phytotoxic Radulanin A Facilitated by the Photochemical Ring Expansion of a 2,2-Dimethylchromene in Flow

Bruce Lockett-Walters et al.

Summary: This study presents the shortest synthesis method for radulanin A to date, utilizing a less explored photochemical ring expansion reaction. The method has been adapted for larger-scale preparation, enabling biological investigations into the herbicidal properties of this natural product.

ORGANIC LETTERS (2022)

Add to Collection

Article Chemistry, Organic

Visible-Light-Induced Difluoroalkylation of 1-(Allyloxy)-2-(1-arylvinyl)benzenes and 1-(1-Arylvinyl)-2-(vinyloxy)benzenes: Synthesis of Bis-Difluoroalkylated Benzoxepines and 2H-Chromenes

Nengneng Zhou et al.

Summary: A novel visible-light-mediated difluoroalkylation method has been developed for the synthesis of bis-difluoroalkylated benzoxepines and 2H-chromenes. This method offers mild reaction conditions, good regioselectivity, a wide substrate scope, good functional-group compatibility, and late-stage modification.

ORGANIC LETTERS (2022)

Add to Collection

Article Chemistry, Organic

Rhodium-Catalyzed Coordination-Assisted Regioselective and Migratory Three-Point Double Annulation of o-Alkenyl Phenols with Tertiary Propargyl Alcohols

Attunuri Nagireddy et al.

Summary: We have developed a new synthetic method for the selective construction of naphtho furan derivatives. This method enables the formation of two new rings and four new bonds in one reaction without the need for any additives. The mechanism of the reaction has been elucidated through labeled and control experiments, revealing the crucial role of a tertiary hydroxyl group in controlling the regioselective insertion of an alkyne and driving the ring expansion via selective olefin reshuffling. The scalable protocol also demonstrates tolerance for late stage functionalization of natural products.

ORGANIC LETTERS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Visible-Light Photocatalyzed peri-(3+2) Cycloadditions of Quinolines

Peter Bellotti et al.

Summary: This study presents a unique method for the one-step synthesis of aza-acenaphthenes through peri-(3 + 2) cycloaddition of simple quinolines with alkynes. A commercial iridium complex is used as a dual-function photosensitizer and photoredox catalyst, enabling a cyclization/rearomatization cascade. The method demonstrates excellent regio- and diastereoselectivity when applied to 8-substituted quinolines and phenanthrolines.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Assembly of Complex 1,4-Cycloheptadienes by (4+3) Cycloaddition of Rhodium(II) and Gold(I) Non-Acceptor Carbenes

Helena Armengol-Relats et al.

Summary: The formal (4+3) cycloaddition of 1,3-dienes with Rh(II) and Au(I) non-acceptor vinyl carbenes leads to a variety of complex and diverse 1,4-cycloheptadienes featuring different substitution patterns. The mechanism involves vinylcyclopropanation/Cope rearrangement or a direct (4+3) cycloaddition by Au(I) and Rh(II) non-acceptor vinyl carbenes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Electrooxidative Rhodium-Catalyzed [5+2] Annulations via C-H/O-H Activations

Yulei Wang et al.

Summary: The study introduces the first electrochemical metal-catalyzed [5+2] cycloadditions, assembling seven-membered benzoxepine skeletons with a high substrate scope and efficiency. The mechanistic studies support a rhodium(III/I) regime involving a benzoxepine-coordinated rhodium(I) sandwich complex as the catalyst resting state.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Review Chemistry, Multidisciplinary

Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings

Rosalie S. Doerksen et al.

Summary: This article summarizes ruthenium-catalyzed cycloadditions to form five-, six-, and seven-membered rings, with a focus on applications in natural product total synthesis. The content is organized by ring size and reaction type, emphasizing processes that involve the formation of at least one C-C bond. Processes involving stoichiometric ruthenium, dehydrogenative condensation-reduction, s-bond activation-initiated annulations without net reduction of bond multiplicity, and photochemically promoted ruthenium-catalyzed cycloadditions are not covered.

CHEMICAL REVIEWS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Intermolecular [5+2] Annulation between 1-Indanones and Internal Alkynes by Rhodium-Catalyzed C-C Activation

Rui Zhang et al.

Summary: The study presents a [5+2] cycloaddition reaction catalyzed by Rh, which activates C-C bonds to enable the cyclization of 1-indanones and internal alkynes. The reaction demonstrates tolerance towards various functional groups and provides a direct route to diverse benzocycloheptenones. DFT studies suggest that migration insertion is the turnover-limiting step, with beneficial pi-pi interactions in the transition states.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis of quaternary carbon-centered indolo[1,2-a]quinazolinones and indazolo[1,2-a]indazolones via C-H functionalization

Kongkona Gogoi et al.

Summary: The unprecedented Ru(ii)-catalyzed Csp(2)-H bond activation and annulation reaction of phenylindazolones with diaryl-substituted alkynes and dialkyl-substituted alkynes provided efficient routes for the construction of all-carbon quaternary-centered indolo[1,2-a]quinazolinones and quaternary carbon-centered indazolo[1,2-a]indazolones, respectively. The formation of indolo[1,2-a]quinazolinones involved Csp(2)-H activation, alkyne insertion, and a 1,2-phenyl shift, while the formation of indazolo[1,2-a]indazolones occurred through a cascade reaction via the formation of exocyclic double bonds containing indolo[1,2-a]quinazolinones.

CHEMICAL COMMUNICATIONS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Chemical Equivalent of Arene Monooxygenases: Dearomative Synthesis of Arene Oxides and Oxepines

Zohaib Siddiqi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Add to Collection

Article Chemistry, Multidisciplinary

Palladium(ii)-catalyzed vinylic geminal double C-H activation and alkyne annulation reaction: synthesis of pentafulvenes

Jyotshna Phukon et al.

CHEMICAL COMMUNICATIONS (2020)

Add to Collection

Article Chemistry, Applied

Practical, Large-Scale Preparation of Benzoxepines and Coumarins through Rhodium(III)-Catalyzed C-H Activation/Annulation Reactions

Moises Gulias et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2019)

Add to Collection

Article Chemistry, Organic

[4+2]-Cycloaddition and 1,4-Addition of ortho-Quinone Methides by a Chiral Crotyl Silane

Christopher R. Wong et al.

ORGANIC LETTERS (2019)

Add to Collection

Article Chemistry, Medicinal

Lead Optimization of Benzoxepin-Type Selective Estrogen Receptor (ER) Modulators and Downregulators with Subtype-Specific ER alpha and ER beta Activity

Niamh M. O'Boyle et al.

JOURNAL OF MEDICINAL CHEMISTRY (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Cp*Co(III)-Catalyzed oxidative [5+2] annulation: regioselective synthesis of 2-aminobenzoxepines via C-H/O-H functionalization of 2-vinylphenols with ynamides

Xiang-Lei Han et al.

CHEMICAL COMMUNICATIONS (2018)

Add to Collection

Article Chemistry, Organic

Synthesis of Spiroketals by Synergistic Gold and Scandium Catalysis

Man Liang et al.

ORGANIC LETTERS (2017)

Add to Collection

Article Chemistry, Multidisciplinary

A Vinyl-Cation-Induced 1,3-Aryl Shift

Liang Fu et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Add to Collection

Article Chemistry, Organic

Base-Promoted Formal [4+3] Annulation between 2-Fluorophenylacetylenes and Ketones: A Route to Benzoxepines

Lu Ouyang et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Facile Generation and Isolation of π-Allyl Complexes from Aliphatic Alkenes and an Electron-Deficient Rh(III) Complex: Key Intermediates of Allylic C-H Functionalization

Yu Shibata et al.

ORGANOMETALLICS (2016)

Add to Collection

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Inverse-Electron-Demand Oxa-Diels-Alder Reaction of In Situ Generated ortho-Quinone Methides with 3-Methyl-2-Vinylindoles

Jia-Jia Zhao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Add to Collection

Article Chemistry, Organic

Synthesis of Phenyl-1-benzoxepinols Isolated from Butcher's Broom and Analogous Benzoxepines

Josef M. Herrmann et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2014)

Add to Collection

Article Chemistry, Multidisciplinary

Straightforward Assembly of Benzoxepines by Means of a Rhodium(III)-Catalyzed C-H Functionalization of o-Vinylphenols

Andres Seoane et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis of Azepine Derivatives by Silver-Catalyzed [5+2] Cycloaddition of γ-Amino Ketones with Alkynes

Ming-Bo Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Add to Collection

Review Chemistry, Multidisciplinary

[5+2] Cycloaddition Reactions in Organic and Natural Product Synthesis

Kai E. O. Ylijoki et al.

CHEMICAL REVIEWS (2013)

Add to Collection

Article Chemistry, Multidisciplinary

Catalyst-Controlled Divergent C-H Functionalization of Unsymmetrical 2-Aryl Cyclic 1,3-Dicarbonyl Compounds with Alkynes and Alkenes

Johnathon D. Dooley et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Add to Collection

Article Chemistry, Organic

Total Synthesis of Bauhinoxepin J: A Biologically Active Dibenzo[b,f]oxepin Isolated from Bauhinia purpurea

Koichi Narita et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2011)

Add to Collection

Article Plant Sciences

Cytotoxic flavaglines and bisamides from Aglaia edulis

Soyoung Kim et al.

JOURNAL OF NATURAL PRODUCTS (2006)

Add to Collection

Review Chemistry, Organic

Recent developments in the synthesis of oxepines

Nicole L. Snyder et al.

TETRAHEDRON (2006)

Add to Collection

Article Chemistry, Organic

Janoxepin and brevicompanine B:: antiplasmodial metabolites from the fungus Aspergillus janus

K Sprogoe et al.

TETRAHEDRON (2005)

Add to Collection

© Peeref 2019-2024. All rights reserved.