18684-94-1

Usage

InChI:InChI=1/C9H9ClO/c1-11-7-9(10)8-5-3-2-4-6-8/h2-7H,1H3/b9-7-

Upstream product

• 691-38-3 (Z)-4-methyl-2-pentene 
• 91309-65-8 3-chloro-3-(p-methoxybenzyl)diazirine 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 3167-62-2 diethyl (dichloromethyl)phosphonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 28540-81-0 (E) 2-iodo-1-chloroethylene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 880634-12-8 5-[(chloromethyl)sulfonyl]-1-phenyl-1H-tetrazole 
• 156-60-5 trans-1,2-dichloroethylene 
• 156-59-2 cis-1,2-Dichloroethylene 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 593-71-5 Chloroiodomethane 
• 2746-25-0 p-Methoxybenzyl bromide 

Downstream Products

• 4705-34-4 1,2-bis(4-methoxyphenyl)ethene 
• 1042728-02-8 (E)-1-(4-methoxystyryl)-1H-imidazole 
• 1058667-06-3 C₁₇H₁₅NO 
• 1058667-09-6 C₁₈H₁₅NO₂ 
• 1058667-04-1 C₁₃H₁₃NO 
• 104151-26-0 trans-1-methoxy-4-(2-cyclohexylethenyl)benzene 
• 171743-15-0 (E)-1-methoxy-4-[2-(4-methylbenzene)sulfonylvinyl]benzene 
• 122395-75-9 Pd{1,1'-bis(diphenylphosphino)ferrocene}(η2-ClCH=CHC6H4OCH3) 

Relevant academic research and scientific papers

Iron-Catalyzed Regioselective Alkenylboration of Olefins

The first examples of an iron-catalyzed three-component synthesis of homoallylic boronates from regioselective union of bis(pinacolato)diboron, an alkenyl halide (bromide, chloride or fluoride), and an olefin are disclosed. Products that bear tertiary or quaternary carbon centers could be generated in up to 87 % yield as single regioisomers with complete retention of the olefin stereochemistry. With cyclopropylidene-containing substrates, ring cleavage leading to trisubstituted E-alkenylboronates were selectively obtained. Mechanistic studies revealed reaction attributes that are distinct from previously reported alkene carboboration pathways.

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.

Continuous Flow Chlorination of Alkenyl Iodides Promoted by Copper Tubing

A simple continuous flow synthesis of alkenyl chlorides from the corresponding readily available alkenyl iodides in copper reactor tubing is described. A variety of alkenyl chlorides were obtained in good to excellent yields with full retention of the dou

HALOGEN-CONTAINING METATHESIS CATALYSTS AND METHODS THEREOF

The present disclosure provides compounds, compositions, and methods for preparing alkenyl halides and/or haloalkyl-substituted olefins with Z-selectivity. The methods are particularly useful for preparing alkenyl fluorides such as CF3-substituted olefins by means of cross-metathesis reactions using halogen-containing molybdenum and tungsten complexes.

Molybdenum chloride catalysts for Z-selective olefin metathesis reactions

The development of catalyst-controlled stereoselective olefin metathesis processes has been a pivotal recent advance in chemistry. The incorporation of appropriate ligands within complexes based on molybdenum, tungsten and ruthenium has led to reactivity and selectivity levels that were previously inaccessible. Here we show that molybdenum monoaryloxide chloride complexes furnish higher-energy (Z) isomers of trifluoromethyl-substituted alkenes through cross-metathesis reactions with the commercially available, inexpensive and typically inert Z-1,1,1,4,4,4-hexafluoro-2-butene. Furthermore, otherwise inefficient and non-stereoselective transformations with Z-1,2-dichloroethene and 1,2-dibromoethene can be effected with substantially improved efficiency and Z selectivity. The use of such molybdenum monoaryloxide chloride complexes enables the synthesis of representative biologically active molecules and trifluoromethyl analogues of medicinally relevant compounds. The origins of the activity and selectivity levels observed, which contradict previously proposed principles, are elucidated with the aid of density functional theory calculations.

METATHESIS CATALYSTS AND METHODS THEREOF

The present application provides, among other things, compounds and methods for metathesis reactions. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and/or stereoselectivity. In some embodim

Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis

Single-electron transmetalation via photoredox/nickel dual catalysis provides the opportunity for the construction of Csp3-Csp2 bonds through the transfer of alkyl radicals under very mild reaction conditions. A general procedure for the cross-coupling of primary and secondary (bis-catecholato)alkylsilicates with alkenyl halides is presented. The developed method allows not only alkenyl bromides and iodides but also previously underexplored alkenyl chlorides to be employed. (Chemical Equation Presented).

Organic photoredox catalysis for the oxidation of silicates: Applications in radical synthesis and dual catalysis

Metal free photooxidation of alkyl bis(catecholato)silicates with the organic dye 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyano-benzene (4CzIPN) allows the smooth formation of alkyl radicals. The latter can be efficiently engaged either with radical acceptors to provide homolytic addition products or in photoredox/nickel dual catalysis reactions to obtain cross-coupling products.

A General Copper-Catalyzed Vinylic Halogen Exchange Reaction

An efficient and general system for the halogen exchange reaction in alkenyl halides has been developed. Upon reaction with catalytic amounts of copper iodide and trans-N,N′-dimethylcyclohexane-1,2-diamine in the presence of tetramethylammonium chloride or bromide, a wide range of easily accessible alkenyl iodides can be smoothly transformed to their far less available chlorinated and brominated derivatives in excellent yields and with full retention of the double bond geometry. This reaction also enables the chlorination of bromoalkenes and could be extended to the use of gem-dibromoalkenes.

Development of a general copper-catalyzed vinylic Finkelstein reaction—application to the synthesis of the C1–C9 fragment of laingolide B

An efficient and broadly applicable procedure for the copper-catalyzed vinylic Finkelstein reaction is reported. Using a simple, readily available and cheap catalytic system, a broad range of alkenyl iodides and bromides can be smoothly converted to their lower homologues with high yields and full retention of the double bond geometry. Key features of this vinylic Finkelstein reaction are its broad applicability, enabling the conversion of readily available alkenyl iodides to their less available brominated and chlorinated counterparts, and the mild reaction conditions compatible with a range of highly functionalized substrates. The potential of this vinylic halogen exchange reaction in total synthesis and medicinal chemistry was demonstrated by its successful use for the synthesis of the C1–C9 fragment of laingolide B and for the late-stage modification of drug-like molecules. The extension of this halogen exchange to the acetylenic and allenic Finkelstein reactions is also reported.