40115-02-4

Upstream product

• 3400-45-1 cyclopentanecarboxylic acid 
• 137-07-5 2-amino-benzenethiol 
• 95-16-9 1,3-Benzothiazole 
• 33240-34-5 cyclopentylmagnesium bromide 
• 7144-49-2 2-methanesulfonylbenzothiazole 
• 137-43-9 Cyclopentyl bromide 
• 615-22-5 2-methylmercaptobenzothiazole 
• 136-95-8 2-amino-benzthiazole 
• 287-92-3 Cyclopentane 
• 872-53-7 cyclopentanealdehyde 
• 51769-43-8 2-(methylthio)naphtho[1,2-d]thiazole 
• 32916-51-1 cyclopentylmagnesium chloride 

Downstream Products

• 175610-95-4 3-(benz-1,3-thiazol-2-yl)cyclopentan-1-ol 

Relevant academic research and scientific papers

Photoelectrochemical cross-dehydrogenative coupling of benzothiazoles with strong aliphatic C-H bonds

A photoelectrochemical strategy for the cross-dehydrogenative coupling of unactivated aliphatic hydrogen donors (e.g.alkanes) with benzothiazoles is reported. We used tetrabutylammonium decatungstate as the photocatalyst to activate strong C(sp3)-H bonds in the chosen substrates, while electrochemistry scavenged the extra electrons.

Desulfonative photoredox alkylation of: N -heteroaryl sulfones-an acid-free approach for substituted heteroarene synthesis

Minisci-type alkylation of electron-deficient heteroarenes has been a pivotal technique for medicinal chemists in the synthesis of drug-like molecules. However, such transformations usually require harsh conditions (e.g., strong acids, stoichiometric amou

Introduction of Heteroaromatic Bases onto Cycloalkanes with BPO

Heteroaromatic bases, such as lepidine, phenanthridine, isoquinoline, etc., were treated with cycloalkanes, such as cyclopentane, cyclohexane, cycloheptane, cyclooctane, etc., under warming conditions with benzoyl peroxide (BPO) to form heteroaromatic bases bearing cycloalkyl groups in good yields. Here, the inert C(sp3)-H bond of cycloalkanes could be functionalized to C(sp3)-heteroaromatic bases via an oxidative radical reaction pathway under transition-metal-free conditions.

Mn(II)-catalyzed C-H alkylation of imidazopyridines and N-heteroarenes via decarbonylative and cross-dehydrogenative coupling

A Mn(II)-catalyzed efficient C-H alkylation of imidazoheterocycles and N-heteroarenes with aliphatic aldehydes has been developed via oxidative decarbonylation. Other alkylating agents such as cyclic alkanes, ethers, and alcohols also coupled with N-heteroarenes through cross-dehydrogenative coupling. Regioselectively C5-alkylated imidazoheterocycles were synthesized in good yields. Experimental results show that radical pathway might be involved in this reaction.

Ni-Catalyzed Reductive Liebeskind-Srogl Alkylation of Heterocycles

Herein we present a Ni-catalyzed alkylation of C-SMe with alkyl bromides for the decoration of heterocyclic frameworks. The protocol, reminiscent to the Liebeskind-Srogl coupling, makes use of simple C(sp2)-SMe to be engaged in a reductive coupling. The reaction is suitable for a preponderance of highly valuable heterocyclic motifs. In addition to cyclic bromides, noncyclic alkyl bromides are well accommodated with exquisite levels of retention over isomerization. The protocol is scalable and permits orthogonal couplings in the presence of other functionalization handles.

Photoredox-Mediated Direct Cross-Dehydrogenative Coupling of Heteroarenes and Amines

A photoredox-mediated direct cross-dehydrogenative coupling reaction to accomplish α-aminoalkylation of N-heteroarenes is reported. This mild reaction has a broad substrate scope, offers the first general method for synthesis of aminoalkylated N-heteroarenes without the need for substrate prefunctionalization, and is scalable to the gram level. Furthermore, the reaction was found to be applicable to other hydrogen donors besides amines (i.e., ethers, an aldehyde, a formamide, p-xylene, and alkanes), thus enabling the preparation of N-heteroarenes bearing various types of substituents.

Silver-mediated 2-arylation/alkylation/acylation of benzothiazoles with aldehydes in water

An efficient and environmentally benign method was developed for the facile synthesis of various 2-aryl and 2-alkyl substituted benzothiazoles in moderate to good yields, using a silver-mediated redox condensation of benzothiazoles and aldehydes in water. Furthermore, this method is also applicable to prepare 2-acyl benzothiazoles.

Nickel-catalyzed coupling of thiomethyl-substituted 1,3-benzothiazoles with secondary alkyl Grignard reagents

Synthetic methods: The Ni-catalyzed alkylation of 2-(methylthio) benzothiazoles through C-S bond cleavage is reported. Reactions with various secondary alkyl nucleophiles proceeded efficiently in the presence of 1,3-butadiene as an additive. This reaction was proposed to proceed by σ-bond metathesis between the thioether and a bis(π-allyl)nickel complex or by an addition/elimination mechanism involving the C=34;N double bond of the benzothiazoles (see scheme). Copyright

Nickel catalyzed alkylation of N-aromatic heterocycles with Grignard reagents through direct C-H bond functionalization

A novel protocol for nickel-catalyzed direct sp2 C-H bond alkylation of N-aromatic heterocycles has been developed. This new reaction proceeded efficiently at room temperature using a Grignard reagent as the coupling partner. This approach prov

Microbial hydroxylation of 2-cycloalkylbenzoxazoles. Part II. Determination of product structures and enhancement of enantiomeric excess

The determinations of product structures obtained in the microbial hydroxylations of various 2-cycloalkyl-1,3-benzoxazoles using Cunninghamella blakesleeana DSM 1906 and Bacillus megaterium DSM 32 are described. The initially low e.e of 3-(benz-1,3-oxazol