{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,10]],"date-time":"2026-10-10T04:17:48Z","timestamp":1791605868833,"version":"4.3.4"},"reference-count":79,"publisher":"Wiley","issue":"52","license":[{"start":{"date-parts":[[2025,8,14]],"date-time":"2025-08-14T00:00:00Z","timestamp":1755129600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2025,8,14]],"date-time":"2025-08-14T00:00:00Z","timestamp":1755129600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2025,9,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The chemoselective reduction of flavones to flavanones remains a significant synthetic challenge in the total synthesis of bioactive flavonoid glycosides. This chemoselective reduction of flavone olefin requires precise control over reactivity to reduce the conjugated \u03b1,\u03b2\u2010unsaturated carbonyl system without affecting the functional groups commonly present in the complex carbohydrate derivatives. We report a straightforward copper\u2010catalyzed reduction method using ammonia borane (NH\n                    <jats:sub>3<\/jats:sub>\n                    \u2022BH\n                    <jats:sub>3<\/jats:sub>\n                    ) as a hydrogen source. The catalytic system, based on a Cu(II) combination with bipyridine ligand, exhibited highly chemoselective hydrogenation of the C\u2550C bond in the enone moiety of flavones to flavanones, whereas the Cu(I) without ligand reduced both functional groups to furnish flavanols. Notably, this methodology demonstrated a broad substrate scope with a wide range of functional group tolerance, including various sugar\u2010derived substituents. The synthetic utility and versatility of the protocol were further highlighted through the useful synthesis of a library of mono\u2010 and disaccharide\u2010conjugated flavonoid glycosides. Interestingly, this catalytic system displayed distinct reactivity by efficiently reducing carbonyl compounds to alcohols while inhibiting over\u2010reduction to alkanes. Additionally, we performed a series of control experiments to gain a deeper insight into the mechanism and revealed that the reaction proceeds through the in situ generation of CuH in the reaction.\n                  <\/jats:p>","DOI":"10.1002\/chem.202502101","type":"journal-article","created":{"date-parts":[[2025,8,14]],"date-time":"2025-08-14T14:07:39Z","timestamp":1755180459000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Copper\u2010catalyzed Chemoselective Reduction of \u03b1,\u03b2\u2010unsaturated Flavone Olefin and It's Glycosides"],"prefix":"10.1002","volume":"31","author":[{"given":"Debabrata","family":"Giri","sequence":"first","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology, Hyderabad  Kandi\u2010502284, Sangareddy Hyderabad Telangana India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"family":"Raghuvendra","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology, Hyderabad  Kandi\u2010502284, Sangareddy Hyderabad Telangana India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ananya","family":"Saha","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology, Hyderabad  Kandi\u2010502284, Sangareddy Hyderabad Telangana India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vulli Sri","family":"Manikanta","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology, Hyderabad  Kandi\u2010502284, Sangareddy Hyderabad Telangana India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9870-7420","authenticated-orcid":false,"given":"Abhijit","family":"Sau","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology, Hyderabad  Kandi\u2010502284, Sangareddy Hyderabad Telangana India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,8,14]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf403332e"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.4c07456"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf5038163"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.0c06132"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/np400929g"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.4c00878"},{"key":"e_1_2_8_7_1","unstructured":"\u201cIdentification of Plasma and Urinary Metabolites and Catabolites Derived from Orange Juice (Poly)phenols: Analysis by High\u2010Performance Liquid Chromatography\u2013High\u2010Resolution Mass Spectrometry | Journal of Agricultural and Food Chemistry \u201d can be found underhttps:\/\/pubs.acs.org\/doi\/10.1021\/acs.jafc.6b02088 n.d."},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf8006568"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1080\/1040869059096"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1FO02664J"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1038\/srep41864"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-022-10661-7"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2OB00038E"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c03863"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB01004D"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c01063"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201502475"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c01248"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c03870"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1340466"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c01357"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b01162"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1RA01672E"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2021.153480"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.1c07557"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja070394v"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja511149y"},{"key":"e_1_2_8_28_1","author":"Leinung W.","year":"2025","journal-title":"J. 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