208838-29-3

Upstream product

• 30780-19-9 4-(4-nitrophenyl)butan-2-one 
• 208838-30-6 2-bromo-4-(4-nitrophenyl)butane 
• 636-98-6 p-nitrobenzene iodide 

Downstream Products

• 208838-30-6 2-bromo-4-(4-nitrophenyl)butane 

Relevant academic research and scientific papers

Metal-Organic Capsules with NADH Mimics as Switchable Selectivity Regulators for Photocatalytic Transfer Hydrogenation

Switchable selective hydrogenation among the groups in multifunctional compounds is challenging because selective hydrogenation is of great interest in the synthesis of fine chemicals and pharmaceuticals as a result of the importance of key intermediates. Herein, we report a new approach to highly selectively (>99%) reducing C=X (X = O, N) over the thermodynamically more favorable nitro groups locating the substrate in a metal-organic capsule containing NADH active sites. Within the capsule, the NADH active sites reduce the double bonds via a typical 2e- hydride transfer hydrogenation, and the formed excited-state NAD+ mimics oxidize the reductant via two consecutive 1e- processes to regenerate the NADH active sites under illumination. Outside the capsule, nitro groups are highly selectively reduced through a typical 1e- hydrogenation. By combining photoinduced 1e- transfer regeneration outside the cage, both 1e- and 2e- hydrogenation can be switched controllably by varying the concentrations of the substrates and the redox potential of electron donors. This promising alternative approach, which could proceed under mild reaction conditions and use easy-to-handle hydrogen donors with enhanced high selectivity toward different groups, is based on the localization and differentiation of the 2e- and 1e- hydrogenation pathways inside and outside the capsules, provides a deep comprehension of photocatalytic microscopic reaction processes, and will allow the design and optimization of catalysts. We demonstrate the advantage of this method over typical hydrogenation that involves specific activation via well-modified catalytic sites and present results on the high, well-controlled, and switchable selectivity for the hydrogenation of a variety of substituted and bifunctional aldehydes, ketones, and imines.

Redox chain reaction - Indole and pyrrole alkylation with unactivated secondary alcohols

Secondary role: Indole and pyrrole derivatives are alkylated with unactivated secondary aliphatic alcohols by a Bronsted acid-catalyzed redox chain reaction mechanism. Broad functional-group tolerance has been demonstrated and preliminary studies suggest that 1,4-reduction of a putative indolyl carbocation is the dominant mechanistic pathway. Copyright

Mechanistic studies of an antibody-catalyzed elimination reaction

Catalytic antibody 43D4-3D12, which was generated against the substituted tertiary amine 1, catalyzes the elimination of HF from β- fluoroketone 2. We have cloned and produced the antibody as a chimeric Fab and constructed a model of the active site-substrate complex. Mutagenesis studies of the active site indicate that Glu(H)50 acts as the general base and suggest that Tyr96(L) may also play a role in the elimination reaction. Antibody 43D4-3D12 also efficiently catalyzes the elimination of HBr from substrate 4 by an E2 mechanism, again involving selective abstraction of the proton β-to the nitrophenyl ring by Glu(H)50. The antibody-catalyzed reaction affords predominantly the internal olefins, whereas the major product resulting from the uncatalyzed reaction is the alcohol, which arises from the competing substitution reaction. In addition, antibody 43D43D12 catalyzes an acetal hydrolysis reaction in which Glu(H)50 likely acts as a general acid. These studies point to the Success of this particular hapten design strategy in generating an active site with a desired catalytic functional group. They also illustrate the utility of using related reactions as mechanistic probes of biological catalysis.