33598-75-3

Upstream product

• 402-43-7 p-trifluoromethylphenyl bromide 
• 411235-57-9 cyclopropylboronic acid 
• 75-11-6 diiodomethane 
• 402-50-6 1-trifluoromethyl-4-vinyl-benzene 
• 75-09-2 dichloromethane 

Relevant academic research and scientific papers

The copper-catalyzed ring-opening reactions of cyclopropanes by N-fluorobenzenesulfonimide toward N-allylsulfonamides

In this paper, we reported a copper-catalyzed ring-opening reaction of arylcyclopropanes by N-fluorobenzenesulfonimide, leading to N-allylsulfonamides in moderate to good yields. This procedure tolerated bromo, fluoro, trifluoromethyl, phenyl and alkyl groups in the phenyl, proceeding with a sequential ring-opening of arylcyclopropanes, and copper-mediated β-H elimination of alkyl radical.

Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes

Cyclopropanes are an important class of building blocks in organic synthesis. Herein, a ring-opening/arylcarboxylation/acylation cascade reaction for the 1,3-difunctionalization of aryl cyclopropanes enabled by cooperative NHC and organophotoredox catalysis is reported. The cascade works on monosubstituted cyclopropanes that are in contrast to the heavily investigated donor–acceptor cyclopropanes more challenging to be difunctionalized. The key step is a radical/radical cross coupling of a benzylic radical generated in the photoredox catalysis cycle with a ketyl radical from the NHC catalysis cycle. The transformation features metal-free reaction conditions and tolerates a diverse range of functionalities.

Lewis Base-Promoted Ring-Opening 1,3-Dioxygenation of Unactivated Cyclopropanes Using a Hypervalent Iodine Reagent

A facile and effective system has been developed for the regio- and chemoselective ring-opening/electrophilic functionalization of cyclopropanes through C?C bond activation by [bis(trifluoroacetoxy)iodo]benzene with the aid of the Lewis basic promoter p-toluenesulfonamide. The p-toluenesulfonamide-promoted system works well for a wide range of cyclopropanes, resulting in the formation of 1,3-diol products in good yields and regioselectivity.

Reductive Cyclopropanations Catalyzed by Dinuclear Nickel Complexes

Dinuclear Ni complexes supported by naphthyridine-diimine (NDI) ligands catalyze the reductive cyclopropanation of alkenes with CH2Cl2 as the methylene source. The use of mild terminal reductants (Zn or Et2Zn) confers significant functional-group tolerance, and the catalyst accommodates structurally and electronically diverse alkenes. Mononickel catalysts bearing related N chelates afford comparatively low cyclopropane yields (≤20 %). These results constitute an entry into catalytic carbene transformations from oxidized methylene precursors.

General and user-friendly protocol for the synthesis of functionalized aryl- and heteroaryl-cyclopropanes by Negishi cross-coupling reactions

The introduction of an unsubstituted cyclopropyl moiety was efficiently accomplished via Negishi cross-coupling of cyclopropylzinc bromide with functionalized aryl halides in high yields and fast reaction rates. The stability and the efficient one-step sy

Suzuki coupling of cyclopropylboronic acid with aryl halides catalyzed by a palladium-tetraphosphine complex

The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)- cyclopentane (Tedicyp) in combination with [Pd(C3H 5)Cl]2 affords a very efficient catalyst for the coupling of cyclopropylboronic acid with aryl bromides and aryl chlorides. Higher reactions rates were observed with aryl bromides than with aryl chlorides; however, even in the presence of 1-0.4% of catalyst, a few aryl chlorides gave the coupling products in good yields. A wide variety of substituents such as alkyl, methoxy, trifluoromethyl, acetyl, benzoyl, formyl, carboxylate, nitro, and nitrile on the aryl halides are tolerated. The coupling reaction of sterically very congested aryl bromides such as bromomesitylene or 2,4,6-triisopropylbromobenzene also proceeds in good yields. Copyright Taylor & Francis LLC.