21777-87-7

Upstream product

• 287-92-3 Cyclopentane 
• 52843-77-3 phenylethynyl trifluoromethyl sulfone 
• 201230-82-2 carbon monoxide 
• 930-51-8 cyclopentylacetylene 
• 536-74-3 phenylacetylene 
• 1253116-91-4 1,1-dibromo-2-cyclopentylethene 
• 98-80-6 phenylboronic acid 
• 1556-18-9 cyclopentyl iodide 
• 137-43-9 Cyclopentyl bromide 
• 930-28-9 cyclopentyl chloride 
• 62781-99-1 cyclopentyl formate 
• 96-41-3 Cyclopentanol 
• 1483-82-5 phenylethynyl chloride 
• 32916-51-1 cyclopentylmagnesium chloride 

Downstream Products

• 1006057-74-4 2-cyclopentyl-3-phenyl-1H-indole-6-carboxylic acid methyl ester 
• 1006057-64-2 3-cyclopentyl-2-phenyl-1H-indole-6-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Enabling the Use of Alkyl Thianthrenium Salts in Cross-Coupling Reactions by Copper Catalysis

Alkyl groups are one of the most widely used groups in organic synthesis. Here, a a series of thianthrenium salts have been synthesized that act as reliable alkylation reagents and readily engage in copper-catalyzed Sonogashira reactions to build C(sp3)?C(sp) bonds under mild photochemical conditions. Diverse alkyl thianthrenium salts, including methyl and disubstituted thianthrenium salts, are employed with great functional breadth, since sensitive Cl, Br, and I atoms, which are poorly tolerated in conventional approaches, are compatible. The generality of the developed alkyl reagents has also been demonstrated in copper-catalyzed Kumada reactions.

Nickel-Catalyzed Sonogashira Coupling Reactions of Nonactivated Alkyl Chlorides under Mild Conditions

The two nickel chlorides1and2with [P,S] and [P,Se] bidentate ligands, respectively, were synthesized and used as catalysts for Sonogashira coupling reaction. Both1and2are efficient catalysts for Sonogashira C(sp3)-C(sp) coupling reactions. Comp

Boryl Radical-Mediated C?H Activation of Inactivated Alkanes for the Synthesis of Internal Alkynes

An intriguing pyridine-boryl radical-mediated C?H alkynylation reaction of inactivated alkanes was described. The reaction features mild operation condition and wide substrate scope, and affords the corresponding products in moderate to good yields. Notab

Cu-Photoredox-catalyzed C(sp)-C(sp3) coupling of redox-active esters with terminal alkynes

Visible-light-induced C(sp)-C(sp3) coupling of redox-active esters with terminal alkynes has been developed. The activation of carboxylic acids as their redox-active ester derivatives was important for this decarboxylative alkynylation. The strategy established here facilitates the straightforward introduction of triple-bonded functional groups and avoids additional photocatalysts. A wide range of primary, secondary and tertiary acids can be converted into the target products; so this reaction exhibits a broad substrate scope and tolerance of functional groups. Mechanistic experiments suggested that this reaction may undergo a radical process. Under mild reaction conditions, a copper acetylide ligand as a photocatalyst delivered an electron to redox-active ester derivatives, and generated alkyl radicals. The radicals reacted with Cu(ii) to deliver a Cu(iii) complex, and then reductive elimination gave the products.

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.

Redox-Activated Amines in C(sp3)-C(sp) and C(sp3)-C(sp2) Bond Formation Enabled by Metal-Free Photoredox Catalysis

The amino group represents one of the most prevalent structural motifs in organic chemistry. Therefore, application of amines as alkylating agents in synthesis is highly compelling. Herein, we present a metal-free photoredox strategy for the formation of C(sp3)-C(sp) and C(sp3)-C(sp2) bonds from redox-activated primary amine derivatives. The developed reaction of 2,4,6-triphenylpyridinium salts with alkynyl p-tolylsulfones, leading to functionalized alkynes, is easily scalable and offers broad substrate scope, high chemoselectivity, and mild conditions. Its potential is also highlighted by diversification of complex molecular scaffolds. Additionally, the approach is also suitable for synthesis of (E)-alkenes from vinyl phenyl sulfones. Mechanistic studies contribute to the elucidation of unexpected differences in reactivity of primary and secondary alkyl substituted pyridinium salts.

Photosensitizer-Free Visible-Light-Mediated Gold-Catalyzed 1,2-Difunctionalization of Alkynes

Under visible-light irradiation, the gold-catalyzed intermolecular difunctionalization of alkynes with aryl diazonium salts in methanol affords a variety of α-aryl ketones in moderate to good yields. In contrast to previous reports on gold-catalyzed reactions that involve redox cycles, no external oxidants or photosensitizers are required. The reaction proceeds smoothly under mild reaction conditions and shows broad functional-group tolerance. Further applications of this method demonstrate the general applicability of the arylation of a vinyl gold intermediate instead of the commonly used protodemetalation step. This step provides facile access to functionalized products in one-pot processes. With a P,N-bidentate ligand, a stable aryl gold(III) species was obtained, which constitutes the first direct experimental evidence for the commonly postulated direct oxidative addition of an aryl diazonium salt to a pyridine phosphine gold(I) complex.

Decarboxylative Alkynylation and Carbonylative Alkynylation of Carboxylic Acids Enabled by Visible-Light Photoredox Catalysis

Visible-light-induced photocatalytic decarboxylative alkynylations of carboxylic acids have been developed for the first time. The reaction features extremely mild conditions, broad substrate scope, and avoids additional oxidants. Importantly, a decarboxy

Nickel-catalyzed sonogashira reactions of non-activated secondary alkyl bromides and iodides

A nicked reaction: The title reaction of terminal alkynes with non-activated secondary alkyl iodides and bromides was accomplished for the first time. This reaction provides a new and practical approach for the synthesis of substituted alkynes (see scheme; cod=cyclo-1,5-octadiene). Copyright

Tandem suzuki-miyaura cross-coupling/dehydrobromination of 1,1-dibromoalkenes to alkynes with a cyclobutene-1,2-diylbis(imidazolium) salt as catalyst precursor

A cyclobutene-1,2-bis(imidazolium) salt proved to be an efficient catalyst precursor for one-pot tandem Suzuki-Miyaura/dehydrobromination reactions for the synthesis of alkynes starting from 1,1-dibromoalkenes and palladium(II) acetate, aryl boronic acids, and potassium tert-butoxide in toluene. Starting materials were prepared from aldehydes under Corey-Fuchs conditions. Georg Thieme Verlag Stuttgart New York.