Construction of 3-Methyl-2-Substituted Benzo[b]furans and 3-Methyl-2-Substituted Benzo[b]thiophenes Using Solid Calcium Carbide as a Substitute for Gaseous Acetylene

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(10), С. 7182 - 7186

Опубликована: Май 2, 2024

A concise method for the facile construction of 3-methyl-2-substituted benzo[b]furans and benzo[b]thiophenes using low-cost, abundant, easy-to-use solid calcium carbide instead flammable explosive gaseous acetylene as an original alkyne source, o-bromophenyl ethers or thioethers substrates through intramolecular carbanion-yne cyclization in a 5-exo-dig manner, subsequent double-bond isomerization is described. The simultaneous formation two C–C bonds realized one-step route. wide substrate scope, high yield, simple workup manipulations are also merits this method. synthetic strategy can be suitable gram scale.

Язык: Английский

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Copper‐Catalyzed Regiodivergent Asymmetric Difunctionalization of Terminal Alkynes

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Июнь 25, 2024

We herein describe the first example of ligand-controlled, copper-catalyzed regiodivergent asymmetric difunctionalization terminal alkynes through a cascade hydroboration and hydroallylation process. The catalytic system, consisting (R)-DTBM-Segphos CuBr, could efficiently achieve 1,1-difunctionalization aryl alkynes, while ligand switching to (S,S)-Ph-BPE result in 1,2-difunctionalization exclusively. In addition, alkyl substituted especially industrially relevant acetylene propyne, were also valid feedstocks for 1,1-difunctionalization. This protocol is characterized by good functional group tolerance, broad scope substrates (>150 examples), mild reaction conditions. showcase value this method late-stage functionalization complicated bioactive molecules simplifying synthetic routes toward key intermediacy natural product (bruguierol A). Mechanistic studies combined with DFT calculations provide insight into mechanism origins ligand-controlled regio- stereoselectivity.

Язык: Английский

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Biomass- and calcium carbide-based recyclable polymers

Green Chemistry, Год журнала: 2021, Номер 23(6), С. 2487 - 2495

Опубликована: Янв. 1, 2021

A series of biomass-derived alcohols were successfully vinylated with calcium carbide followed by the polymerization. The polymers tested as materials and disassembled back to monomers through pyrolysis.

Язык: Английский

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Generation, regeneration, and recovery of Cu catalytic system by changing the polarity of electrodes

Green Chemistry, Год журнала: 2022, Номер 24(3), С. 1132 - 1140

Опубликована: Янв. 1, 2022

An electric current promotes copper electrode dissolution in ionic liquids and creates an active catalyst. The catalyst formed was successfully tested synthetic transformations. Reversing the polarity allows regeneration of ILs

Язык: Английский

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Construction of Pyrazolo[1,5-a]pyrimidines and Pyrimido[1,2-b]indazoles with Calcium Carbide as an Alkyne Source

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(28), С. 5822 - 5826

Опубликована: Янв. 1, 2024

One-step construction of both 5-arylpyrazolo[1,5- a ]pyrimidines and 2-arylpyrimido[1,2- b ]indazoles using inexpensive, abundant easy-to-handle calcium carbide as solid alkyne source is depicted.

Язык: Английский

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Acetylene and Ethylene: Universal C2 Molecular Units in Cycloaddition Reactions

Synthesis, Год журнала: 2021, Номер 54(04), С. 999 - 1042

Опубликована: Сен. 27, 2021

Abstract Acetylene and ethylene are the smallest molecules that contain an unsaturated carbon–carbon bond can be efficiently utilized in a large variety of cycloaddition reactions. In this review, we summarize application these C2 molecular units chemistry highlight their amazing synthetic opportunities. 1 Introduction 2 Fundamental Features Differences Cycloaddition Reactions Involving Ethylene 3 (2+1) 4 [2+2] 5 (3+2) 6 [4+2] 7 (2+2+1) 8 [2+2+2] 9 The Use for Deuterium 13C Labeling 10 Conclusions

Язык: Английский

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A sustainable polymer and coating system based on renewable raw materials

Green Chemistry, Год журнала: 2022, Номер 24(24), С. 9772 - 9780

Опубликована: Янв. 1, 2022

A complete biobased process towards polymers and coatings using starting materials derived from renewable resources implementing sustainable synthetic steps.

Язык: Английский

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Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas

ACS Catalysis, Год журнала: 2023, Номер 13(16), С. 10751 - 10755

Опубликована: Авг. 1, 2023

Acetylene gas is an important feedstock for chemical production, although it underutilized in organic synthesis. We have developed intermolecular gold(I)-catalyzed alkyne/alkene reaction of o-allylphenols with acetylene that gives rise to chromanes by a stereospecific aryloxycyclization through the nucleophilic regioselective opening cyclopropyl gold(I)-carbene intermediates. The synthetic application this method was demonstrated late-stage functionalization natural product lapachol.

Язык: Английский

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Highly Stereoselective Synthesis of 2-Acyl-3-sulfonamidobut-2-enoates Using Solid Calcium Carbide as a Substitute for Gaseous Acetylene

Organic Letters, Год журнала: 2024, Номер 26(29), С. 6269 - 6273

Опубликована: Июль 17, 2024

Multifunctional group compounds, 2-acyl-3-sulfonamidobut-2-enoates, are efficiently constructed using solid calcium carbide as an alkyne source through the simultaneous formation of two bonds in one step. The salient features this protocol use inexpensive, abundant, and easy-to-use a substitute for flammable explosive gaseous acetylene, low-cost catalyst, mild conditions, wide substrate scope, high stereoselectivity, satisfactory yield, simple manipulation. This method can also be extended to gram scale.

Язык: Английский

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One-step construction of indolo[2,1- a ]isoquinolines using solid calcium carbide as an alternative to gaseous acetylene

Synthetic Communications, Год журнала: 2024, Номер 54(14), С. 1209 - 1219

Опубликована: Июль 17, 2024

Язык: Английский

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