91335-74-9

Upstream product

• 108-90-7 chlorobenzene 
• 142-29-0 cyclopentene 
• 29540-84-9 4-chlorophenyl trifluoromethanesulfonate 
• 106-48-9 4-chloro-phenol 
• 106-39-8 bromochlorobenzene 
• 137-43-9 Cyclopentyl bromide 
• 149683-48-7 tricyclopentylindium(III) 
• 89523-62-6 (4-chlorophenyl)zinc(II) chloride 
• 17151-48-3 tributyl(4-chlorophenyl)stannane 

Relevant academic research and scientific papers

Modular Functionalization of Arenes in a Triply Selective Sequence: Rapid C(sp2) and C(sp3) Coupling of C?Br, C?OTf, and C?Cl Bonds Enabled by a Single Palladium(I) Dimer

Full control over multiple competing coupling sites would enable straightforward access to densely functionalized compound libraries. Historically, the site selection in Pd0-catalyzed functionalizations of poly(pseudo)halogenated arenes has been unpredictable, being dependent on the employed catalyst, the reaction conditions, and the substrate itself. Building on our previous report of C?Br-selective functionalization in the presence of C?OTf and C?Cl bonds, we herein complete the sequence and demonstrate the first general arylations and alkylations of C?OTf bonds (in I dimer. This allowed the realization of the first general and triply selective sequential C?C coupling (in 2D and 3D space) of C?Br followed by C?OTf and then C?Cl bonds.

A Versatile Route to Unstable Diazo Compounds via Oxadiazolines and their Use in Aryl–Alkyl Cross-Coupling Reactions

Coupling of readily available boronic acids and diazo compounds has emerged recently as a powerful metal-free carbon–carbon bond forming method. However, the difficulty in forming the unstable diazo compound partner in a mild fashion has hitherto limited their general use and the scope of the transformation. Here, we report the application of oxadiazolines as precursors for the generation of an unstable family of diazo compounds using flow UV photolysis and their first use in divergent protodeboronative and oxidative C(sp2)?C(sp3) cross-coupling processes, with excellent functional-group tolerance.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Alkyl Bromides: Et3N as the Terminal Reductant

Reductive cross-coupling has emerged as a direct method for the construction of carbon-carbon bonds. Most cobalt-, nickel-, and palladium-catalyzed reductive cross-coupling reactions to date are limited to stoichiometric Mn(0) or Zn(0) as the reductant. One nickel-catalyzed cross-coupling paradigm using Et3N as the terminal reductant is reported. By using this photoredox catalysis and nickel catalysis approach, a direct Csp2-Csp3 reductive cross-coupling of aryl bromides with alkyl bromides is achieved under mild conditions without stoichiometric metal reductants.

Highly selective palladium-catalyzed oxidative Csp2-Csp 3 cross-coupling of arylzinc and alkylindium reagents through double transmetallation

Using desyl chloride (2-chloro-1,2-diphenylethanone) as the oxidant, the palladium-catalyzed reaction of arylzinc with alkylindium reagents occurred smoothly in a highly selective manner to afford the products in 57-90% yields. Preliminary kinetic data in

Stille cross-couplings of unactivated secondary alkyl halides using monoorganotin reagents

The first catalyst that achieves Stille cross-couplings of secondary (as well as primary) alkyl halides has been developed. The method employs easily handled and inexpensive catalyst components (NiCl2 and 2,2′-bipyridine) and, through the use of monoorganotin reagents, avoids the formation of toxic and difficult-to-remove triorganotin side products. Copyright