{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,26]],"date-time":"2026-10-26T06:23:01Z","timestamp":1792995781745,"version":"4.5.0"},"reference-count":141,"publisher":"Wiley","issue":"38","license":[{"start":{"date-parts":[[2025,7,16]],"date-time":"2025-07-16T00:00:00Z","timestamp":1752624000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2025,7,16]],"date-time":"2025-07-16T00:00:00Z","timestamp":1752624000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22471074"],"award-info":[{"award-number":["22471074"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004106","name":"East China Normal University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004106","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["advanced.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Advanced Science"],"published-print":{"date-parts":[[2025,10]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Herein, a palladium\u2010catalyzed coupling of\n                    <jats:italic>gem<\/jats:italic>\n                    \u2010iododiborylalkanes with electron\u2010rich olefins to access \u03b2,\u03b2\u2010diboryl ketones and aldehydes under mild conditions is reported. This method exhibits broad substrate scope and excellent functional group tolerance. Mechanistic studies support a distinctive pathway involving\n                    <jats:italic>gem<\/jats:italic>\n                    \u2010diboryl carbon\u2010centered radicals and a Pd(0)\/Pd(I) catalytic cycle, without the formation of Pd(II) intermediates. This protocol provides a new platform for accessing synthetically valuable\n                    <jats:italic>gem<\/jats:italic>\n                    \u2010diboryl carbonyl compounds and expands the reactivity profile of organoboron\u2010based radical transformations.\n                  <\/jats:p>","DOI":"10.1002\/advs.202508566","type":"journal-article","created":{"date-parts":[[2025,7,17]],"date-time":"2025-07-17T02:25:06Z","timestamp":1752719106000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Palladium\u2010Catalyzed\n                    <i>Gem<\/i>\n                    \u2010Diborylalkylation of Silyl Enol Ethers and\n                    <i>N<\/i>\n                    \u2010Vinylacetamide via Diboryl Carbon\u2010Centered Radicals"],"prefix":"10.1002","volume":"12","author":[{"given":"Xiao\u2010Yu","family":"Xie","sequence":"first","affiliation":[{"name":"Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and Molecular Engineering East China Normal University  3663 N Zhongshan Road Shanghai 200062 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yi","family":"Wei","sequence":"additional","affiliation":[{"name":"Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and Molecular Engineering East China Normal University  3663 N Zhongshan Road Shanghai 200062 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin\u2010Yi","family":"Chen","sequence":"additional","affiliation":[{"name":"Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and Molecular Engineering East China Normal University  3663 N Zhongshan Road Shanghai 200062 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ming","family":"Li","sequence":"additional","affiliation":[{"name":"Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and Molecular Engineering East China Normal University  3663 N Zhongshan Road Shanghai 200062 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7341-4931","authenticated-orcid":false,"given":"Kai","family":"Hong","sequence":"additional","affiliation":[{"name":"Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and Molecular Engineering East China Normal University  3663 N Zhongshan Road Shanghai 200062 China"},{"name":"Shanghai Frontiers Science Center of Molecule Intelligent Syntheses School of Chemistry and Molecular Engineering East China Normal University  3663 N Zhongshan Road Shanghai 200062 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,7,16]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC08027A"},{"key":"e_1_2_7_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201901600"},{"key":"e_1_2_7_1_3","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201901503"},{"key":"e_1_2_7_1_4","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202207067"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01501a029"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201712186"},{"key":"e_1_2_7_2_3","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b08282"},{"key":"e_1_2_7_2_4","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201907962"},{"key":"e_1_2_7_2_5","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201916340"},{"key":"e_1_2_7_2_6","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202107665"},{"key":"e_1_2_7_2_7","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202004581"},{"key":"e_1_2_7_2_8","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202113333"},{"key":"e_1_2_7_2_9","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2022.10.010"},{"key":"e_1_2_7_2_10","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2023.04.006"},{"key":"e_1_2_7_2_11","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202307540"},{"key":"e_1_2_7_2_12","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202418651"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b03893"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aal3803"},{"key":"e_1_2_7_3_3","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b10519"},{"key":"e_1_2_7_3_4","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201711390"},{"key":"e_1_2_7_3_5","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201802384"},{"key":"e_1_2_7_3_6","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201906497"},{"key":"e_1_2_7_3_7","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b07960"},{"key":"e_1_2_7_3_8","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c07964"},{"key":"e_1_2_7_3_9","doi-asserted-by":"publisher","DOI":"10.1039\/D1QO00169H"},{"key":"e_1_2_7_3_10","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202309566"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202000603"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202202646"},{"key":"e_1_2_7_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202405898"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202400340"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202303175"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/D4SC06514J"},{"key":"e_1_2_7_6_3","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5c00469"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)92984-X"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.6023\/cjoc202207030"},{"key":"e_1_2_7_7_3","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c03804"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1055\/a-2036-1151"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201701390"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB02978K"},{"key":"e_1_2_7_9_3","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2018.04.061"},{"key":"e_1_2_7_9_4","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00953A"},{"key":"e_1_2_7_9_5","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC01048D"},{"key":"e_1_2_7_9_6","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.1c02496"},{"key":"e_1_2_7_9_7","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.1c00455"},{"key":"e_1_2_7_9_8","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c03418"},{"key":"e_1_2_7_9_9","doi-asserted-by":"publisher","DOI":"10.1039\/D1QO01300A"},{"key":"e_1_2_7_9_10","doi-asserted-by":"publisher","DOI":"10.1016\/j.cclet.2022.108048"},{"key":"e_1_2_7_9_11","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.202300349"},{"key":"e_1_2_7_9_12","doi-asserted-by":"publisher","DOI":"10.1038\/s41570-024-00650-x"},{"key":"e_1_2_7_9_13","doi-asserted-by":"publisher","DOI":"10.1039\/D3CC06165E"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202209079"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c02510"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202315227"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202315232"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/cjoc.202400840"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202210532"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202415301"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202401396"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5c00638"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202305175"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202401050"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c02261"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c04018"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5c00730"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41570-021-00284-3"},{"key":"e_1_2_7_22_1","volume":"146","author":"Garwood J. J. A.","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-08-052349-1.00042-1"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1973.1011"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00831a019"},{"key":"e_1_2_7_24_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303192"},{"key":"e_1_2_7_24_4","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303914"},{"key":"e_1_2_7_24_5","first-page":"997","volume-title":"Comprehensive Asymmetric Catalysis I\u2010III","author":"Carreira E. M.","year":"2000"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00832a031"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00072a006"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.202300038"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.6023\/cjoc202402007"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0719428"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201101861"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201406450"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201915814"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aav3200"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC08077E"},{"key":"e_1_2_7_29_3","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b04699"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)80489-5"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(92)89041-A"},{"key":"e_1_2_7_30_3","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1992.2099"},{"key":"e_1_2_7_30_4","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b05058"},{"key":"e_1_2_7_30_5","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b01230"},{"key":"e_1_2_7_30_6","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b03587"},{"key":"e_1_2_7_30_7","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b03700"},{"key":"e_1_2_7_30_8","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202008435"},{"key":"e_1_2_7_30_9","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC06341J"},{"key":"e_1_2_7_30_10","doi-asserted-by":"publisher","DOI":"10.1039\/D1QO00648G"},{"key":"e_1_2_7_30_11","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-022-01092-y"},{"key":"e_1_2_7_30_12","doi-asserted-by":"publisher","DOI":"10.1039\/D3SC04549H"},{"key":"e_1_2_7_30_13","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c08984"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol901359n"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.2174\/1570178614666170321114445"},{"key":"e_1_2_7_31_3","doi-asserted-by":"publisher","DOI":"10.1039\/C8QO00513C"},{"key":"e_1_2_7_31_4","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-021-1054-4"},{"key":"e_1_2_7_31_5","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202301826"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.3c01915"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202302638"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00479a061"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0021060"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2005.01.176"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/om00128a038"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00545a045"},{"key":"e_1_2_7_36_3","doi-asserted-by":"publisher","DOI":"10.1021\/om50005a008"},{"key":"e_1_2_7_36_4","doi-asserted-by":"publisher","DOI":"10.1021\/cr00097a009"},{"key":"e_1_2_7_36_5","doi-asserted-by":"publisher","DOI":"10.1021\/jo4013942"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1971"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja505455z"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201603329"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC03731G"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00347K"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b01469"},{"key":"e_1_2_7_40_3","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00226B"},{"key":"e_1_2_7_40_4","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00044"},{"key":"e_1_2_7_40_5","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201813523"},{"key":"e_1_2_7_40_6","doi-asserted-by":"publisher","DOI":"10.1246\/cl.190006"},{"key":"e_1_2_7_40_7","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00403"},{"key":"e_1_2_7_40_8","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202311972"},{"key":"e_1_2_7_40_9","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.4c00815"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)96431-2"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19880000563"},{"key":"e_1_2_7_41_3","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob25990g"},{"key":"e_1_2_7_41_4","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201308534"},{"key":"e_1_2_7_41_5","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201712775"},{"key":"e_1_2_7_41_6","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c09716"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja075245r"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2091883"},{"key":"e_1_2_7_42_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201311323"},{"key":"e_1_2_7_42_4","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC00297K"},{"key":"e_1_2_7_42_5","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201409617"},{"key":"e_1_2_7_42_6","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201706554"},{"key":"e_1_2_7_42_7","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b10009"},{"key":"e_1_2_7_42_8","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b03591"},{"key":"e_1_2_7_42_9","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c03993"},{"key":"e_1_2_7_42_10","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c03239"},{"key":"e_1_2_7_42_11","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-021-21270-9"}],"container-title":["Advanced Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/advs.202508566","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/advs.202508566","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/advs.202508566","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,3,9]],"date-time":"2026-03-09T19:33:48Z","timestamp":1773084828000},"score":1,"resource":{"primary":{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/10.1002\/advs.202508566"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,7,16]]},"references-count":141,"journal-issue":{"issue":"38","published-print":{"date-parts":[[2025,10]]}},"alternative-id":["10.1002\/advs.202508566"],"URL":"https:\/\/doi.org\/10.1002\/advs.202508566","archive":["Portico"],"relation":{},"ISSN":["2198-3844","2198-3844"],"issn-type":[{"value":"2198-3844","type":"print"},{"value":"2198-3844","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,7,16]]},"assertion":[{"value":"2025-05-12","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-07-16","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e08566"}}