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Here, we prepared one low Ru loading catalyst (Ru\n                    <jats:sub>0.8<\/jats:sub>\n                    \/C) for RCF of biomass to selectively produce different lignin oils (both monomers and oligomers) under different reaction atmospheres. The yield of phenolic monomers reached 46.0wt.% (rich in 4\u2010propylguaiacol and 4\u2010propylsyringol) in the RCF of birch wood under high H\n                    <jats:sub>2<\/jats:sub>\n                    pressure and using methanol as the solvent. But, under N\n                    <jats:sub>2<\/jats:sub>\n                    atmosphere the dominant monomers shifted to 4\u2010(prop\u20101\u2010enyl)guaiacol and 4\u2010(prop\u20101\u2010enyl)syringol (79.6% selectivity) with 35.8wt.% yield of total monomers using the same catalyst. The developed catalyst can also transform native lignin in other biomasses such as pine and corn stover. Mechanistic investigation using different model compounds and deuteration indicates that removal of the C\n                    <jats:sub>\u03b3<\/jats:sub>\n                    \u2500OH in methanol\u2010extracted lignin fragments occurred before obtaining the monomeric lignin fragment, and the C\n                    <jats:sub>\u03b1<\/jats:sub>\n                    \u2500OH and \u03b2\u2500O\u25004 bonds were then cleaved simultaneously to form 4\u2010(prop\u20101\u2010enyl) substituted monomers. The results are distinct from the reported mechanism that the precursors of the propyl and prop\u20101\u2010enyl substituted monomers are monolignols with removal of the C\n                    <jats:sub>\u03b3<\/jats:sub>\n                    \u2500OH at the monomeric level. Thus, this work provided novel insights into the reaction pathway of (native) lignin depolymerization.\n                  <\/jats:p>","DOI":"10.1002\/anie.202502545","type":"journal-article","created":{"date-parts":[[2025,4,7]],"date-time":"2025-04-07T15:42:04Z","timestamp":1744040524000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":25,"title":["Reductive Catalytic Fractionation of Lignocellulose Toward Propyl\u2010 or Propenyl\u2010Substituted Monomers and Mechanistic Understanding"],"prefix":"10.1002","volume":"64","author":[{"given":"Haiyun","family":"Huang","sequence":"first","affiliation":[{"name":"Key Laboratory of Renewable Energy Guangzhou Institute of Energy Conversion Chinese Academy of Sciences  Guangzhou 510640 P.R. China"},{"name":"School of Energy Science and Engineering University of Science and Technology of China  Guangzhou 510640 P.R. 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China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,4,21]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00155"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201510351"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00566K"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.2c00664"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aau1567"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1246843"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0EE02870C"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.4c00087"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.3c01309"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.9b04837"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3EE00965C"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5EE00204D"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201903526"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201710838"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aaf7810"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-018-0148-8"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.202200365"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacsau.3c00092"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cej.2023.142225"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jechem.2024.01.003"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7GC02989F"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.joule.2022.08.005"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.202300103"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2RE00275B"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201402017"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-024-49812-x"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41893-023-01201-w"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10086-004-0670-y"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c04028"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.8b04032"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2GC03777G"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202307116"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7GC03417B"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201802497"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c03393"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.xcrp.2021.100567"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-32451-5"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.3c05461"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.4c03184"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cej.2022.138179"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1GC00503K"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7GC01324H"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-021-00783-2"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.apcatb.2021.120767"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/jz201182w"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b00556"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8GC01031E"},{"key":"e_1_2_8_48_1","unstructured":"National 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