135871-64-6Relevant articles and documents
Copper-catalyzed hydroformylation and hydroxymethylation of styrenes
Franke, Robert,Geng, Hui-Qing,Meyer, Tim,Wu, Xiao-Feng
, p. 14937 - 14943 (2021/12/02)
Hydroformylation catalyzed by transition metals is one of the most important homogeneously catalyzed reactions in industrial organic chemistry. Millions of tons of aldehydes and related chemicals are produced by this transformation annually. However, most of the applied procedures use rhodium catalysts. In the procedure described here, a copper-catalyzed hydroformylation of alkenes has been realized. Remarkably, by using a different copper precursor, the aldehydes obtained can be further hydrogenated to give the corresponding alcohols under the same conditions, formally named as hydroxymethylation of alkenes. Under pressure of syngas, various aldehydes and alcohols can be produced from alkenes with copper as the only catalyst, in excellent regioselectivity. Additionally, an all-carbon quaternary center containing ethers and formates can be synthesized as well with the addition of unactivated alkyl halides. A possible reaction pathway is proposed based on our results. This journal is
Practical synthesis of pharmaceutically relevant molecules enriched in sp3 character
Campbell, Peter S.,Jamieson, Craig,Simpson, Iain,Watson, Allan J. B.
, p. 46 - 49 (2017/12/27)
The expedient synthesis of compounds enriched in sp3 character is key goal in modern drug discovery. Herein, we report how a single pot Suzuki-Miyaura-hydrogenation can be used to furnish lead and fragment-like products in good to excellent yields. The approach has been successfully applied in formats amenable to parallel synthesis, in an asymmetric sense, and in the preparation of molecules with annotated biological activity.
Bioconversion of aromatic compounds by Escherichia coli that expresses cytochrome P450 CYP153A13a gene isolated from an alkane-assimilating marine bacterium Alcanivorax borkumensis
Otomatsu, Toshihiko,Bai, Liming,Fujita, Naoya,Shindo, Kazutoshi,Shimizu, Keiko,Misawa, Norihiko
experimental part, p. 234 - 240 (2011/01/03)
The cytochrome P450 CYP153 family has been isolated from alkane-assimilating bacteria. CYP153 has been shown to mediate terminal hydroxylations of linear alkanes or alkyl aromatics. We here performed the biotransformation of various aromatic compounds by Escherichia coli cells that expressed the CYP153A13a (P450balk) gene, which was isolated from an alkane-degading marine bacterium Alcanivorax borkumensis. Aromatic compounds including a short alkyl moiety or methyl ether moiety, and phenolic compounds were converted to their respective hydroxylated products, whose structures were determined by HRMS and NMR analyses. The present study revealed that the catalytic function of CYP153A13a is multifunctional, i.e., it can hydroxylate not only the terminal of short alkyl groups that attached to aromatic rings but also the p-position of phenolic compounds substituted with a halogen or the acetyl group. CYP153A13a was also shown to demethylate methylether-including aromatic compounds.
