Direct synthesis of indazole derivatives via Rh(iii)-catalyzed C–H activation of phthalazinones and allenes

2021 ◽  
Vol 19 (35) ◽  
pp. 7701-7705
Author(s):  
Chuanliu Yin ◽  
Tianshuo Zhong ◽  
Xiangyun Zheng ◽  
Lianghao Li ◽  
Jian Zhou ◽  
...  
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Direct Synthesis ◽  
Atom Economy

An Rh(iii)-catalyzed annulation of phthalazinones and various allenes was developed, leading to the formation of indazole derivatives. This catalytic system exhibits excellent functional group tolerance and atom economy.

scholarly journals Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols

2011 ◽  
Vol 7 ◽  
pp. 1198-1204 ◽  
Author(s):  
Michel Chiarucci ◽  
Mirko Locritani ◽  
Gianpiero Cera ◽  
Marco Bandini
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Direct Synthesis ◽  
Catalytic Process ◽  
Primary Alcohols

Gold(I)-N-heterocyclic carbene (NHC) complexes proved to be a reliable catalytic system for the direct synthesis of functionalized γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with primary alcohols. Good isolated chemical yields were obtained for a range of malonyl and acetate derivatives. The good performance in reagent-grade solvents and the functional group/moisture tolerance make this catalytic process a promising route for the synthesis of architecturally complex polycyclic structures.

Differentiation and Functionalization of Adjacent, Remote C–H Bonds

2019 ◽  
Author(s):  
Hang Shi ◽  
Lu Yi ◽  
Jiang Weng ◽  
Katherine Bay ◽  
Xiangyang Chen ◽  
...  
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Hydrocinnamic Acid ◽  
Molecular Architectures ◽  
Site Selective ◽  
Developing Strategies

<p>Site-selective functionalizations of C–H bonds will ultimately afford chemists transformative tools for editing and constructing complex molecular architectures<sup>1-4</sup>. Towards this goal, developing strategies to activate C–H bonds that are distal from a functional group is essential<sup>4-6</sup>. In this context, distinguishing remote C–H bonds on adjacent carbon atoms is an extraordinary challenge due to the lack of electronic or steric bias between the two positions. Herein, we report the design of a catalytic system leveraging a remote directing template and a transient norbornene mediator to selectively activate a previously inaccessible remote C–H bond that is one bond further away. The generality of this approach has been demonstrated with a range of heterocycles, including a complex anti-leukemia agent, and hydrocinnamic acid substrates.</p>

Enantioselective alpha-Arylation of Benzamides via Synergistic Nickel and Metallaphotoredox Catalysis

2019 ◽  
Author(s):  
John Montgomery ◽  
Alexander W. Rand
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Enantiomeric Excess ◽  
New Method ◽  
Aryl Bromides

A new method to access alpha-arylated benzamides has been enabled by metallaphotoredox catalysis. This system allows for non-directed C–H functionalization of N-alkyl benzamides using a dual nickel/iridium catalytic system to form tertiary stereocenters in good enantiomeric excess and moderate yields. This reaction shows excellent functional group compatibility and can be performed using a number of sterically and electronically different aryl bromides and secondary benzamides.

Enantioselective alpha-Arylation of Benzamides via Synergistic Nickel and Metallaphotoredox Catalysis

2019 ◽  
Author(s):  
John Montgomery ◽  
Alexander W. Rand
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Enantiomeric Excess ◽  
New Method ◽  
Aryl Bromides

A new method to access alpha-arylated benzamides has been enabled by metallaphotoredox catalysis. This system allows for non-directed C–H functionalization of N-alkyl benzamides using a dual nickel/iridium catalytic system to form tertiary stereocenters in good enantiomeric excess and moderate yields. This reaction shows excellent functional group compatibility and can be performed using a number of sterically and electronically different aryl bromides and secondary benzamides.

C(sp3)–H Functionalization with Isocyanides

2021 ◽  
Author(s):  
Weixiang Wang ◽  
Tianqi Liu ◽  
Chang-Hua Ding ◽  
Bin Xu
Keyword(s):  
Functional Group ◽  
Ugi Reaction ◽  
Atom Economy ◽  
Passerini Reaction

Isocyanide is well known for its multi-component reactions (MCR), such as Passerini reaction and Ugi reaction, with diverse molecular skeletons, high functional group compatibility, and good atom economy. With the...

Rh(III)-catalyzed annulated coupling of sulfoxonium ylides and iodonium ylides: a rapid access to isocoumarins

2022 ◽  
Author(s):  
Chuanliu Yin ◽  
Lianghao Li ◽  
Chuanming Yu
Keyword(s):  
Functional Group ◽  
Direct Synthesis ◽  
Rapid Access ◽  
Iodonium Ylides

Direct synthesis of isocoumarin skeletons has been realized through Rh(III)-Catalyzed [3 + 3] annulation of sulfoxonium ylides and iodonium carbenes. The synthetic protocol constructed efficiently with the broad functional group...

Difunctionalization of the Isocyano Group: Atom-Economic ­Synthesis of Pyrimidinediones

Synlett ◽  
2018 ◽  
Vol 30 (03) ◽  
pp. 252-256 ◽  
Author(s):  
Jian Lang ◽  
Ye Wei
Keyword(s):  
Late Stage ◽  
Functional Group ◽  
Structural Diversity ◽  
Synthetic Methods ◽  
Chemical Bonds ◽  
Atom Economy

The exploration of synthetic methods involving the formation of new chemical bonds at both the nitrogen and carbons atoms of the isocyano group would largely enrich the structural diversity of compounds. Herein, we disclosed a silver-catalyzed difunctionalization of the isocyano group with cyclic oximes. This method can generate a great array of structurally novel and interesting pyrimidinediones and features excellent atom economy, good functional group compatibility, and amenability to late-stage modifications.

Direct Oxidation of Primary Alcohols to Carboxylic Acids

Synthesis ◽  
2020 ◽  
Author(s):  
Travis J. Williams ◽  
Valeriy Cherepakhin
Keyword(s):  
Carboxylic Acids ◽  
Direct Synthesis ◽  
Primary Alcohol ◽  
Alcohol Oxidation ◽  
Atom Economy ◽  
Primary Alcohols ◽  
Direct Oxidation ◽  
Metal Compounds ◽  
New Methods ◽  
Active Research

AbstractOxidation of primary alcohols to carboxylic acids is a fundamental transformation in organic chemistry, yet despite its simplicity, extensive use, and relationship to pH, it remains a subject of active research for synthetic organic chemists. Since 2013, a great number of new methods have emerged that utilize transition-metal compounds as catalysts for acceptorless dehydrogenation of alcohols to carboxylates. The interest in this reaction is explained by its atom economy, which is in accord with the principles of sustainability and green chemistry. Therefore, the methods for the direct synthesis of carboxylic acids from alcohols is ripe for a modern survey, which we provide in this review.1 Introduction2 Thermodynamics of Primary Alcohol Oxidation3 Oxometalate Oxidation4 Transfer Dehydrogenation5 Acceptorless Dehydrogenation6 Electrochemical Methods7 Outlook

Electrophilic Amination with Anthranils through Thioamide-Assisted Cobalt(III)-Catalyzed C(sp3)–H Activation

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3881-3890
Author(s):  
Jie Li ◽  
Lei Liu ◽  
Zhao Zhang ◽  
Yucheng Wang ◽  
Yan Zhang
Keyword(s):  
Late Stage ◽  
Functional Group ◽  
Atom Economy ◽  
Electrophilic Amination ◽  
Amino Aldehydes ◽  
Mild Conditions ◽  
Weakly Coordinating

Cobalt(III)-catalyzed electrophilic amination of inert C(sp3)–H bonds of weakly coordinating thioamides with readily accessible anthranil derivatives was accomplished under mild conditions, with good functional group tolerance, thus providing various amino aldehydes and amino ketones. Moreover, our protocol with the versatile [Cp*Co(MeCN)3][SbF6]2 features excellent atom-economy and oxidant-free conditions, and allows facile late-stage functionalization.

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