5888-51-7Relevant articles and documents
Electrochemical Benzylic C(sp3)-H Isothiocyanation
Guo, Weisi,Li, Ming,Li, Yufeng,Wang, Tao,Wen, Lirong,Zhang, Shanxue
supporting information, p. 1742 - 1746 (2022/03/14)
Selective C(sp3)-H isothiocyanation represents a significant strategy for the synthesis of isothiocyanate derivatives. We report herein an electrochemical benzylic isothiocyanation in a highly chemo- and site-selective manner under external oxidant-free conditions. The high chemoselectivity is attributed to the facile in situ isomerization of benzylic thiocyanates to isothiocyanates. Notably, the method exhibits high functional group compatibility and is suitable for late-stage functionalization of bioactive molecules.
Photocatalytic Upgrading of Lignin Oil to Diesel Precursors and Hydrogen
Dou, Zhaolin,Wang, Min,Zhang, Zhe,Zhou, Hongru
supporting information, p. 16399 - 16403 (2021/06/27)
Producing renewable biofuels from biomass is a promising way to meet future energy demand. Here, we demonstrated a lignin to diesel route via dimerization of the lignin oil followed by hydrodeoxygenation. The lignin oil undergoes C?C bond dehydrogenative coupling over Au/CdS photocatalyst under visible light irradiation, co-generating diesel precursors and hydrogen. The Au nanoparticles loaded on CdS can effectively restrain the recombination of photogenerated electrons and holes, thus improving the efficiency of the dimerization reaction. About 2.4 mmol gcatal?1 h?1 dimers and 1.6 mmol gcatal?1 h?1 H2 were generated over Au/CdS, which is about 12 and 6.5 times over CdS, respectively. The diesel precursors are finally converted into C16–C18 cycloalkanes or aromatics via hydrodeoxygenation reaction using Pd/C or porous CoMoS catalyst, respectively. The conversion of pine sawdust to diesel was performed to demonstrate the feasibility of the lignin-to-diesel route.
Site-Selective Alkoxylation of Benzylic C?H Bonds by Photoredox Catalysis
Lee, Byung Joo,DeGlopper, Kimberly S.,Yoon, Tehshik P.
supporting information, p. 197 - 202 (2019/11/26)
Methods that enable the direct C?H alkoxylation of complex organic molecules are significantly underdeveloped, particularly in comparison to analogous strategies for C?N and C?C bond formation. In particular, almost all methods for the incorporation of alcohols by C?H oxidation require the use of the alcohol component as a solvent or co-solvent. This condition limits the practical scope of these reactions to simple, inexpensive alcohols. Reported here is a photocatalytic protocol for the functionalization of benzylic C?H bonds with a wide range of oxygen nucleophiles. This strategy merges the photoredox activation of arenes with copper(II)-mediated oxidation of the resulting benzylic radicals, which enables the introduction of benzylic C?O bonds with high site selectivity, chemoselectivity, and functional-group tolerance using only two equivalents of the alcohol coupling partner. This method enables the late-stage introduction of complex alkoxy groups into bioactive molecules, providing a practical new tool with potential applications in synthesis and medicinal chemistry.
