57918-63-5

Upstream product

• 588-73-8 (Z)-β-bromostyrene 
• 932-88-7 1-iodo-2-phenylethyne 
• 130274-37-2 1-(4-methoxybenzyl)-2,4-bis(trimethylsilyl)cyclopentane 
• 75-47-8 iodoform 
• 100-52-7 benzaldehyde 
• 3020-28-8 (iodomethyl)triphenylphosphonium iodide 
• 19319-11-0 (Z)-1-phenyl-2-(trimethylsilyl)ethylene 
• 187874-76-6 ((Z)-1-Bromo-2-phenyl-vinyl)-bis-(1,2-dimethyl-propyl)-borane 
• 104-53-0 3-phenyl-propionaldehyde 
• 247943-41-5 2,2-diiodo-1-phenylethyl acetate 
• 60806-00-0 4,4,6-trimethyl-2-styryl-[1,3,2]dioxaborinane 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 536-74-3 phenylacetylene 
• 29949-93-7 iodomethylenetriphenylphosphorane 

Downstream Products

• 19319-11-0 (Z)-1-phenyl-2-(trimethylsilyl)ethylene 
• 503622-58-0 N-(Trifluoromethanesulfonyl)-2-((E)-β-styryl)piperidine 
• 13141-45-2 (Z)-1,4-diphenylbut-1-ene-3-yne 
• 7338-50-3 6-phenylfulvene 
• 130248-52-1 6-phenyl-3-(trimethylsilyl)fulvene 
• 130274-38-3 (E)-1,3-bis(trimethylsilyl)-6-phenylfulvene 
• 5807-76-1 (1Z,3Z)-1,4-diphenylbuta-1,3-diene 
• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 5808-05-9 (1Z,3E)-1,4-diphenylbuta-1,3-diene 
• 100-42-5 styrene 
• 13340-46-0 (2-phenylethyl)triethoxysilane 
• 65119-09-7 (E)-styryl(triethoxy)silane 
• 31915-94-3 (Z)-1-Phenylbuta-1,3-diene 
• 39491-72-0 (Z)-(4-methylpenta-1,3-dien-1-yl)benzene 

Relevant academic research and scientific papers

Copper-catalyzed cross-coupling of amino acid-derived amides with (Z)-vinyl iodides: Unexpected solvent effect and preparation of plocabulin

A copper-catalyzed cross-coupling reaction of amino acid-derived amides and (Z)-vinyl iodide was studied to improve a key step in the synthesis of plocabulin, a novel microtubule destabilizer agent of marine origin. The study revealed a profound solvent effect with 1,2-dimethoxyethane (DME), which gave consistently high yields across a large variety of the amide and (Z)-vinyl iodide substrates. The protocol was successfully utilized in the preparation of plocabulin and provided a significantly improved yield.

Oxidative Addition of Alkenyl and Alkynyl Iodides to a AuI Complex

The first isolated examples of intermolecular oxidative addition of alkenyl and alkynyl iodides to AuI are reported. Using a 5,5′-difluoro-2,2′-bipyridyl ligated complex, oxidative addition of geometrically defined alkenyl iodides occurs readily, reversibly and stereospecifically to give alkenyl-AuIII complexes. Conversely, reversible alkynyl iodide oxidative addition generates bimetallic complexes containing both AuIII and AuI centers. Stoichiometric studies show that both new initiation modes can form the basis for the development of C?C bond forming cross-couplings.

Stereospecific Iron-Catalyzed Carbon(sp2)-Carbon(sp3) Cross-Coupling with Alkyllithium and Alkenyl Iodides

An efficient synthetic protocol involving iron-catalyzed cross-coupling reactions between organolithium compounds and alkenyl iodides as key coupling partners was achieved. More than 30 examples were obtained with moderate to good yields and high stereospecificity. Gram-scale and synthetic applications of this procedure are recorded herein to demonstrate its feasibility and potential utilization.

Cyclic Vinyl(aryl)iodonium Salts: Synthesis and Reactivity

A convenient, highly regioselective synthesis of five-membered cyclic vinyl(aryl)iodonium salts directly from β-iodostyrenes is presented. An X-ray crystal structure confirms the identity of these heterocycles. These λ3-iodanes can be converted

Concise and gram-scale total synthesis of lansiumamides A and B and alatamide

The total synthesis of potent anti-obesity lansiumamide B was accomplished in four steps using commercially available materials. The synthetic strategy, featured with copper-catalyzed Buchwald coupling, is concise, convergent, practical and can be carried out on a one-gram scale. This approach could give either Z- or E-configured enamide moiety in natural products with absolute stereocontrol and was applied in the total synthesis of natural products.

Unveiling the Takai Olefination Reagent via Tris(tert-butoxy)siloxy Variants

The elusive Takai olefination reagent, namely, the iodo-methylidene Cr(III) complex [Cr2Cl4(CHI)(thf)4], has been isolated by careful handling of the reaction between CrCl2and CHI3in THF at ?35 °C. Alternatively, treatment of [Cr(OSi(OtBu)3)2] with CHI3gave the mixed-valent dihalido-methanide complex [CrII/III2I2(OSi(OtBu)3)2(CHI2)], featuring a Cr(III)-CHI2moiety. In the presence of TMEDA nucleophilic attack at CHI2occurred generating the zwitterionic species [CrIII(OSi(OtBu)3)2(tmeda-CHI)][I]. Complexes [Cr2Cl4(CHI)(thf)4] and [CrII/III2I2(OSi(OtBu)3)2(CHI2)] were screened for their ability to induce monohalido olefination of benzaldehyde. Remarkably, both complexes promote olefination, with [Cr2Cl4(CHI)(thf)4] accomplishing the sameEselectivity as Takai’s original mixture. Complex [CrII/III2I2(OSi(OtBu)3)2(CHI2)], however, appeared to give preferentiallyZisomer, corroborating the monoiodo-methylidene species Cr(III)-CHI-Cr(III) as the active olefination component of the originalin situgenerated Takai reagent mixture.

Stereoselective Synthesis of Vinyl Iodides through Copper(I)-Catalyzed Finkelstein-Type Halide-Exchange Reaction

An efficient method for the stereoselective synthesis of vinyl iodides is described. The reactions of vinyl bromides with potassium iodide proceed smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding vinyl iodides stereospecifically and in satisfactory to excellent yields.

Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings

Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.

A New Entry of Practical and Chemoselective Iodocarbenoids for Carbonyl Iodomethylenation

Direct oxidative addition of CHI3 to the Mg-TiCl4 bimetallic species resulted in the generation of a highly chemoselective and practically convenient iodomethylenetitanium complex, which efficiently effected condensation even with enolizable or inert carbonyl compounds, such as sterically congested ketones, to provide vinyl iodide compounds.

Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides

This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy-to-operate nickel-catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional-group tolerance. The nickel-catalytic system displays good chemoselectivity between the two C(sp2)-halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols.