33491-06-4

Upstream product

• 87992-04-9 4-(1,2-dichloro-vinyl)-anisole 
• 41448-64-0 1-(2,2-dichlorovinyl)-4-methoxybenzene 
• 768-60-5 4-methoxyphenylacetylen 
• 64-19-7 acetic acid 
• 3167-62-2 diethyl (dichloromethyl)phosphonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 67-56-1 methanol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 7572-29-4 dichloroethyne 

Downstream Products

• 1314145-18-0 C₁₃H₁₂BrClO 
• 87991-99-9 (Z)-1-(1,2-dichlorovinyl)-4-methoxybenzene 
• 1612219-25-6 tert-butyl((4-methoxyphenyl)ethynyl)sulfane 
• 186345-05-1 (R)-1-chloro-2-hydroxy-2-(p-methoxyphenyl)ethane 
• 186345-05-1 (S)-1-chloro-2-hydroxy-2-(p-methoxyphenyl)ethane 
• 197250-99-0 1-(but-1-yn-1-yl)-4-methoxybenzene 
• 1007597-82-1 N-((4-methoxyphenyl)ethynyl)-N,4-dimethylbenzenesulfonamide 
• 70626-01-6 (Z)-2-Chloro-1-(4-methoxy-phenyl)-3-phenyl-propenone 

Relevant academic research and scientific papers

Method for preparing 1-halogenated alkyne under catalysis of heterogeneous Ag catalyst at room temperature

The invention discloses a novel method for preparing 1-halogenated alkyne under the catalysis of a heterogeneous Ag catalyst at room temperature. The method comprises the steps of mixing terminal alkyne compounds containing different substituent groups, N

Iron-Catalyzed Cross-Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow

Transition-metal-catalyzed cross-coupling chemistry can be regarded as one of the most powerful protocols to construct carbon–carbon bonds. While the field is still dominated by palladium catalysis, there is an increasing interest to develop protocols that utilize cheaper and more sustainable metal sources. Herein, we report a selective, practical, and fast iron-based cross-coupling reaction that enables the formation of Csp?Csp3 and Csp2?Csp3 bonds. In a telescoped flow process, the reaction can be combined with the Grignard reagent synthesis. Moreover, flow allows the use of a supporting ligand to be avoided without eroding the reaction selectivity.

Transition-Metal-Free One-Step Synthesis of Ynamides

A robust transition-metal-free one-step strategy for the synthesis of ynamides from sulfonamides and (Z)-1,2-dichloroalkenes or alkynyl chlorides is presented. This method is not only effective for internal ynamides but also amenable for terminal ynamides. Various functional groups, even the vinyl moiety, are compatible, and thus, this strategy offers the opportunity for further functionalization.

Gold-Catalyzed Highly Chemo- and Regioselective C-H Bond Functionalization of Phenols with Haloalkynes

A highly chemo- and stereoselective addition of unprotected phenols to haloalkynes was developed. A ligand and counterion controlled process enabled the highly site-selective and chemoselective C-H bond functionalization of phenol derivatives with haloalkynes in moderate to excellent yield at room temperature. The simple availability of the starting materials in combination with the preferred para-C-H functionalization over a competing O-H insertion makes this an attractive protocol. The stereoselectivity of the products depends on the choice of the catalyst. From a synthetic prospective, this method offers an efficient route towards vinyl chlorides, which are valuable precursors for the synthesis of pharmaceutical drugs.

Palladium-Catalyzed Decarboxylative γ-Arylation for the Synthesis of Tetrasubstituted Chiral Allenes

An enantiospecific palladium-catalyzed decarboxylative coupling of acyclic β,γ-alkynoic acids with various aryl iodides to chiral tetrasubstituted allenes is described. The coupling reaction comprises a decarboxylative γ-palladation of α,α-disubstituted carboxylic acids to provide the tetrasubstituted allenes with complete point-to-axial chirality transfer in excellent yields.

Manganese-Catalyzed Dual-Deoxygenative Coupling of Primary Alcohols with 2-Arylethanols

Reported herein is a general and efficient dual-deoxygenative coupling of primary alcohols with 2-arylethanols catalyzed by a well-defined Mn/PNP pincer complex. This reaction is the first example of the catalytic dual-deoxygenation of alcohols using a non-noble-metal catalyst. Both deoxygenative homocoupling of 2-arylethanols (17 examples) and their deoxygenative cross-coupling with other primary alcohols (20 examples) proceeded smoothly to form the corresponding alkenes by a dehydrogenation and deformylation reaction sequence.

Au-Catalyzed Intermolecular [2+2] Cycloadditions between Chloroalkynes and Unactivated Alkenes

The [2+2] cycloaddition is a versatile strategy for the synthesis of strained cyclobutenes of high synthetic value. In this study, two efficient intermolecular [2+2] cycloadditions between two different types of chloroalkynes and unactivated alkene are realized with gold catalysis. Of significance is that the reaction works with challenging monosubstituted unactivated alkenes, which is unprecedented in gold catalysis and scarcely documented in other metal-catalyzed/promoted reactions; moreover, the reaction exhibits excellent regioselectivities, which are much better than those reported in literature. With 1,2-disubstituted unactivated alkenes, the reaction is largely stereospecific. The cyclobutene products can be prepared in nearly gram scale and readily undergo further reactions including various cross-coupling reactions using the C(sp2)-Cl and/or C(sp2)-SPh bond, which in turn substantially broaden the scope of accessible cyclobutenes and enhance the synthetic utility of this bimolecular reaction.

Highly efficient and recyclable catalyst for the direct chlorination, bromination and iodination of terminal alkynes

Direct halogenation, including chlorination, bromination and iodination of terminal alkynes, are of great importance in organic synthesis. Here an efficient and recyclable nano-Ag/g-C3N4 catalyst system was developed and proved to be remarkably active with 39 examples varied from chlorination, bromination to iodination, of which 14 runs have yielded more than 95% of the product. Recycling of the catalyst was also achieved without obvious activity loss after several runs: 99% yield was observed even after 5 runs in the bromination of phenylacetylene. The catalysts system is of low cost and easy to be prepared, making this procedure versatile, convenient and economic.

A copper (II) (II) composite chlorinating agent and copper-based composite chlorinating agent synthesis of 1-chloro-2-aryl acetylene method

The invention discloses a copper (II) composite chlorinating agent and a method for synthesizing 1-chlorine-2-aryl acetylene based on the copper (II) composite chlorinating agent. The structural formula of the copper (II) composite chlorinating agent is CuCl2.xNaCl.yAl2O3. The chlorinating agent is applicable to chlorination of various substituted aryl acetylene substrates, and is high in universality; the chlorinating agent can directly carry out chlorination reaction on aryl acetylene so as to obtain a 1-chlorine-2-aryl acetylene product; the method is mild in reaction condition, 1-chlorine-2-aryl acetylene can be synthesized with high yield and high selectivity, and the production cost of the 1-chlorine-2-aryl acetylene derivative is greatly lowered.

Silver-catalyzed synthesis of 1-chloroalkynes directly from terminal alkynes

An efficient method to prepare 1-chloroalkynes was investigated. The method involved the use of readily available terminal alkynes and a catalytic amount of a silver salt with N-chlorosuccinimide as the chlorinating agent under mild conditions. Compared with the existing process, this method has a broad substrate scope: 19 examples were explored, and the products were obtained in excellent yields and were easily isolated by vacuum distillation. Moreover, recycling of the catalyst was achieved by simple filtration and desiccation, which made the method more economic and environmentally benign.