Direct and selective hydrogenolysis of arenols and aryl methyl ethers
For valorization of biomass, the conversion of lignin to deoxygenated bulk aromatic compounds is an emerging subject of interest. Because aromatic rings are susceptible to metal-catalysed hydrogenation, the selective hydrogenolysis of carbon–oxygen bonds still remains a great challenge. Herein we re...
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| Published in | Nature communications Vol. 6; no. 1; p. 6296 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
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Nature Publishing Group UK
23.02.2015
Nature Publishing Group |
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| Abstract | For valorization of biomass, the conversion of lignin to deoxygenated bulk aromatic compounds is an emerging subject of interest. Because aromatic rings are susceptible to metal-catalysed hydrogenation, the selective hydrogenolysis of carbon–oxygen bonds still remains a great challenge. Herein we report direct and selective hydrogenolysis of sp
2
C–OH bonds in substituted phenols and naphthols catalysed by hydroxycyclopentadienyl iridium complexes. The corresponding arenes were obtained in up to 99% yields, indicating the possible production of arenes from lignin-derived bio-oils. Furthermore, the same catalysts were applied to the unprecedented selective hydrogenolysis of the sp
3
C–O bonds in aryl methyl ethers. Thus, the hydrodeoxygenation of vanillylacetone, a lignin model compound, afforded alkylbenzenes as the major products via triple deoxygenation.
Deoxygenating phenols is a difficult task, made more complex by the tendency of hydrogenation techniques to also reduce the aromatic ring. Here, the authors show an iridium catalyst that can selectively cleave the C–O bond in phenols and related compounds, as well as cleaving aryl methyl ethers. |
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| AbstractList | For valorization of biomass, the conversion of lignin to deoxygenated bulk aromatic compounds is an emerging subject of interest. Because aromatic rings are susceptible to metal-catalysed hydrogenation, the selective hydrogenolysis of carbon-oxygen bonds still remains a great challenge. Herein we report direct and selective hydrogenolysis of sp(2) C-OH bonds in substituted phenols and naphthols catalysed by hydroxycyclopentadienyl iridium complexes. The corresponding arenes were obtained in up to 99% yields, indicating the possible production of arenes from lignin-derived bio-oils. Furthermore, the same catalysts were applied to the unprecedented selective hydrogenolysis of the sp(3) C-O bonds in aryl methyl ethers. Thus, the hydrodeoxygenation of vanillylacetone, a lignin model compound, afforded alkylbenzenes as the major products via triple deoxygenation.For valorization of biomass, the conversion of lignin to deoxygenated bulk aromatic compounds is an emerging subject of interest. Because aromatic rings are susceptible to metal-catalysed hydrogenation, the selective hydrogenolysis of carbon-oxygen bonds still remains a great challenge. Herein we report direct and selective hydrogenolysis of sp(2) C-OH bonds in substituted phenols and naphthols catalysed by hydroxycyclopentadienyl iridium complexes. The corresponding arenes were obtained in up to 99% yields, indicating the possible production of arenes from lignin-derived bio-oils. Furthermore, the same catalysts were applied to the unprecedented selective hydrogenolysis of the sp(3) C-O bonds in aryl methyl ethers. Thus, the hydrodeoxygenation of vanillylacetone, a lignin model compound, afforded alkylbenzenes as the major products via triple deoxygenation. For valorization of biomass, the conversion of lignin to deoxygenated bulk aromatic compounds is an emerging subject of interest. Because aromatic rings are susceptible to metal-catalysed hydrogenation, the selective hydrogenolysis of carbon–oxygen bonds still remains a great challenge. Herein we report direct and selective hydrogenolysis of sp 2 C–OH bonds in substituted phenols and naphthols catalysed by hydroxycyclopentadienyl iridium complexes. The corresponding arenes were obtained in up to 99% yields, indicating the possible production of arenes from lignin-derived bio-oils. Furthermore, the same catalysts were applied to the unprecedented selective hydrogenolysis of the sp 3 C–O bonds in aryl methyl ethers. Thus, the hydrodeoxygenation of vanillylacetone, a lignin model compound, afforded alkylbenzenes as the major products via triple deoxygenation. Deoxygenating phenols is a difficult task, made more complex by the tendency of hydrogenation techniques to also reduce the aromatic ring. Here, the authors show an iridium catalyst that can selectively cleave the C–O bond in phenols and related compounds, as well as cleaving aryl methyl ethers. For valorization of biomass, the conversion of lignin to deoxygenated bulk aromatic compounds is an emerging subject of interest. Because aromatic rings are susceptible to metal-catalysed hydrogenation, the selective hydrogenolysis of carbon-oxygen bonds still remains a great challenge. Herein we report direct and selective hydrogenolysis of sp(2) C-OH bonds in substituted phenols and naphthols catalysed by hydroxycyclopentadienyl iridium complexes. The corresponding arenes were obtained in up to 99% yields, indicating the possible production of arenes from lignin-derived bio-oils. Furthermore, the same catalysts were applied to the unprecedented selective hydrogenolysis of the sp(3) C-O bonds in aryl methyl ethers. Thus, the hydrodeoxygenation of vanillylacetone, a lignin model compound, afforded alkylbenzenes as the major products via triple deoxygenation. For valorization of biomass, the conversion of lignin to deoxygenated bulk aromatic compounds is an emerging subject of interest. Because aromatic rings are susceptible to metal-catalysed hydrogenation, the selective hydrogenolysis of carbon-oxygen bonds still remains a great challenge. Herein we report direct and selective hydrogenolysis of sp2 C-OH bonds in substituted phenols and naphthols catalysed by hydroxycyclopentadienyl iridium complexes. The corresponding arenes were obtained in up to 99% yields, indicating the possible production of arenes from lignin-derived bio-oils. Furthermore, the same catalysts were applied to the unprecedented selective hydrogenolysis of the sp3 C-O bonds in aryl methyl ethers. Thus, the hydrodeoxygenation of vanillylacetone, a lignin model compound, afforded alkylbenzenes as the major products via triple deoxygenation. |
| ArticleNumber | 6296 |
| Author | Kusumoto, Shuhei Nozaki, Kyoko |
| Author_xml | – sequence: 1 givenname: Shuhei surname: Kusumoto fullname: Kusumoto, Shuhei organization: Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo – sequence: 2 givenname: Kyoko surname: Nozaki fullname: Nozaki, Kyoko email: nozaki@chembio.t.u-tokyo.ac.jp organization: Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/25704229$$D View this record in MEDLINE/PubMed |
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| References_xml | – reference: ChoiJCleavage of sp3 C–O bonds via oxidative addition of C–H bondsJ. Am. Chem. Soc.200913115627156291:CAS:528:DC%2BD1MXht1Kjtb7J10.1021/ja906930u – reference: SergeevAGHartwigJFSelective, nickel-catalyzed hydrogenolysis of aryl ethersScience20113324394431:CAS:528:DC%2BC3MXkvVamu7k%3D2011Sci...332..439S10.1126/science.1200437 – reference: BlumYCzarkieDRahaminYShvoY(Cyclopentadienone)rutheniuim carbonyl complexes—a new class of homogeneous hydrogenation catalystsOrganometallics19854145914611:CAS:528:DyaL2MXksFCht78%3D10.1021/om00127a027 – reference: van der BoomMELiouS-YDavidYBShimonLJWMilsteinDAlkyl− and aryl−oxygen bond activation in solution by rhodium(I), palladium(II), and nickel(II). transition-metal-based selectivityJ. Am. Chem. Soc.1998120653165411:CAS:528:DyaK1cXktlWgsr8%3D10.1021/ja9738889 – reference: Weissermel K., Arpe H. J. Eds Industrial Organic Chemistry 4th edn Wiley VCH (2003). – reference: CornellaJGómez-BengoaEMartinRCombined experimental and theoretical study on the reductive cleavage of inert C–O bonds with silanes: ruling out a classical Ni(0)/Ni(II) catalytic couple and evidence for Ni(I) intermediatesJ. Am. Chem. Soc.2013135199720091:CAS:528:DC%2BC3sXntVeksw%3D%3D10.1021/ja311940s – reference: FedorovAToutovAASwisherNAGrubbsRHLewis-base silane activation: from reductive cleavage of aryl ethers to selective ortho-silylationChem. Sci.20134164016451:CAS:528:DC%2BC3sXjtlyms7w%3D10.1039/c3sc22256j – reference: LaskarDDYangBWangHLeeJPathways for biomass-derived lignin to hydrocarbon fuelsBiofuels Bioprod. Bioref.201376026261:CAS:528:DC%2BC3sXhtFCkur7M10.1002/bbb.1422 – reference: HerrmannJMKönigBReductive deoxygenation of alcohols: catalytic methods beyond Barton–McCombie deoxygenationEur. J. Org. Chem.20132013701770271:CAS:528:DC%2BC3sXhtFOrsL3F10.1002/ejoc.201300657 – reference: TobisuMYamakawaKShimasakiTChataniNNickel-catalyzed reductive cleavage of aryl–oxygen bonds in alkoxy- and pivaloxyarenes using hydrosilanes as a mild reducing agentChem. Commun.201147294629481:CAS:528:DC%2BC3MXit1ejtrw%3D10.1039/c0cc05169a – reference: MineEHiyoshiNSatoOChandrashekharRVShiraiMSelective hydrogenation of naphthols to tetralones over supported palladium catalysts in supercritical carbon dioxide solventChem. Lett.2006357807811:CAS:528:DC%2BD28XnsVyhsrk%3D10.1246/cl.2006.780 – reference: Álvarez-BercedoPMartinRNi-catalyzed reduction of inert C–O bonds: a new strategy for using aryl ethers as easily removable directing groupsJ. Am. Chem. Soc.2010132173521735310.1021/ja106943q – reference: TuckCOPérezEHorváthITSheldonRAPoliakoffMValorization of biomass: deriving more value from wasteScience20123376956991:CAS:528:DC%2BC38XhtFCktb%2FF2012Sci...337..695T10.1126/science.1218930 – reference: Wuts, P. G. M. & Greene, T. W. in Greene's Protective Groups in Organic Synthesis 3rd edn 367–430Wiley (2006). – reference: NishimuraSOhbuchiSIkenoKOkadaYHydrogenation and hydrogenolysis. XVII. The selectivities of platinum group metals in catalytic hydrogenation of 2-naphthol and tetrahydro-2-naphtholsBull. Chem. Soc. Jpn198457255725641:CAS:528:DyaL2cXlvFSqs7s%3D10.1246/bcsj.57.2557 – reference: RenYYanMWangJZhangZCYaoKSelective reductive cleavage of inert aryl C–O bonds by an iron catalystAngew. Chem. Int. Ed.20135212674126781:CAS:528:DC%2BC3sXhs1WmsbnN10.1002/anie.201305342 – reference: KusumotoSAkiyamaMNozakiKAcceptorless dehydrogenation of C–C single bonds adjacent to functional groups by metal-ligand cooperationJ. Am. Chem. 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| SubjectTerms | 639/638/403/934 639/638/77 Aromatic compounds Ethers Humanities and Social Sciences Iridium multidisciplinary Phenols Science Science (multidisciplinary) |
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| Title | Direct and selective hydrogenolysis of arenols and aryl methyl ethers |
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