{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,29]],"date-time":"2026-07-29T20:48:24Z","timestamp":1785358104411,"version":"3.55.0"},"reference-count":90,"publisher":"Wiley","issue":"46","license":[{"start":{"date-parts":[[2023,7,17]],"date-time":"2023-07-17T00:00:00Z","timestamp":1689552000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP21H04681"],"award-info":[{"award-number":["JP21H04681"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP21K15223"],"award-info":[{"award-number":["JP21K15223"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP23H04912"],"award-info":[{"award-number":["JP23H04912"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP23KJ1346"],"award-info":[{"award-number":["JP23KJ1346"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2023,8,15]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A quadruple N\u2010heterocyclic carbene\/cobalt\/photoredox\/Br\u00f8nsted base catalysis to realize branch\u2010selective hydroacylation of styrenes with aromatic and aliphatic aldehydes is demonstrated. This protocol allows access to branched ketones from readily available materials in an atom\u2010economical manner. The quadruple catalysis can transfer a formyl hydrogen of aldehydes as a hydrogen radical equivalent onto the terminal carbon of an alkene by controlled electron and proton transfers.<\/jats:p>","DOI":"10.1002\/chem.202301484","type":"journal-article","created":{"date-parts":[[2023,6,1]],"date-time":"2023-06-01T07:09:20Z","timestamp":1685603360000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":30,"title":["A Quadruple Catalysis Enabling Intermolecular Branch\u2010Selective Hydroacylation of Styrenes"],"prefix":"10.1002","volume":"29","author":[{"given":"Yunosuke","family":"Takekawa","sequence":"first","affiliation":[{"name":"Division of Pharmaceutical Sciences Graduate School of Medical Sciences Kanazawa University  Kakuma-machi Kanazawa 920-1192 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masanari","family":"Nakagawa","sequence":"additional","affiliation":[{"name":"Institute for Chemical Research Kyoto University  Uji, Kyoto 611-0011 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3141-5279","authenticated-orcid":false,"given":"Kazunori","family":"Nagao","sequence":"additional","affiliation":[{"name":"Institute for Chemical Research Kyoto University  Uji, Kyoto 611-0011 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1374-1137","authenticated-orcid":false,"given":"Hirohisa","family":"Ohmiya","sequence":"additional","affiliation":[{"name":"Institute for Chemical Research Kyoto University  Uji, Kyoto 611-0011 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,7,17]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"For selected reviews and papers on catalytic hydroacylation of alkenes with aldehydes see;"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar2000716"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.202000378"},{"key":"e_1_2_8_4_1","unstructured":"For selected reviews and papers on transition metal-catalyzed hydroacylation of alkenes see;"},{"key":"e_1_2_8_5_2","unstructured":"C.\u2005H. Jun J.\u2005B. Hong D.\u2005Y. Lee Synlett1999 1\u201312;"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900096x"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2sc20350b"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6QO00023A"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1610141"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC02112E"},{"key":"e_1_2_8_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)61854-3"},{"key":"e_1_2_8_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo961887d"},{"key":"e_1_2_8_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00096a037"},{"key":"e_1_2_8_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja980610n"},{"key":"e_1_2_8_15_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.72.303"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol034343o"},{"key":"e_1_2_8_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200352751"},{"key":"e_1_2_8_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200603133"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja107198e"},{"key":"e_1_2_8_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc10683j"},{"key":"e_1_2_8_21_1","unstructured":"For selected papers on branch-selective hydroacylation of alkenes with aldehydes see;"},{"key":"e_1_2_8_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309987"},{"key":"e_1_2_8_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4SC02026J"},{"key":"e_1_2_8_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b00856"},{"key":"e_1_2_8_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b00024"},{"key":"e_1_2_8_26_1","unstructured":"For selected reviews and papers on radical-mediated hydroacylation of alkenes with aldehydes see;"},{"key":"e_1_2_8_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9601425"},{"key":"e_1_2_8_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC02112E"},{"key":"e_1_2_8_29_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1610329"},{"key":"e_1_2_8_30_2","doi-asserted-by":"crossref","unstructured":"H.\u2005S. Dang B.\u2005P. Roberts J. Chem. Soc. Perkin Trans. 1 1998 67\u201375;","DOI":"10.1039\/a704878e"},{"key":"e_1_2_8_31_2","doi-asserted-by":"crossref","unstructured":"S. Tsujimoto T. Iwahama S. Sakaguchi Y. Ishii Chem. Commun.2001 2352\u20132353;","DOI":"10.1039\/b107548a"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c04047"},{"key":"e_1_2_8_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c03315"},{"key":"e_1_2_8_34_1","unstructured":"\u00a0"},{"key":"e_1_2_8_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201903726"},{"key":"e_1_2_8_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr990124y"},{"key":"e_1_2_8_37_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00339K"},{"key":"e_1_2_8_38_1","unstructured":"\u00a0"},{"key":"e_1_2_8_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b00880"},{"key":"e_1_2_8_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b07194"},{"key":"e_1_2_8_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c01199"},{"key":"e_1_2_8_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c02849"},{"key":"e_1_2_8_43_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-021-24144-2"},{"key":"e_1_2_8_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c02639"},{"key":"e_1_2_8_45_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2021.132212"},{"key":"e_1_2_8_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC01538E"},{"key":"e_1_2_8_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c01795"},{"key":"e_1_2_8_48_1","unstructured":"For selected reviews on radical N-heterocyclic carbene catalysis by other groups"},{"key":"e_1_2_8_49_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41570-021-00321-1"},{"key":"e_1_2_8_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c03996"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c00527"},{"key":"e_1_2_8_52_1","unstructured":"For selected reviews and papers on MHAT see;"},{"key":"e_1_2_8_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00334"},{"key":"e_1_2_8_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.8b00337"},{"key":"e_1_2_8_55_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC04112B"},{"key":"e_1_2_8_56_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1QO01139A"},{"key":"e_1_2_8_57_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1610680"},{"key":"e_1_2_8_58_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1989.1071"},{"key":"e_1_2_8_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja048698u"},{"key":"e_1_2_8_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja809842b"},{"key":"e_1_2_8_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja405219f"},{"key":"e_1_2_8_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja5105602"},{"key":"e_1_2_8_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja502885c"},{"key":"e_1_2_8_64_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature14006"},{"key":"e_1_2_8_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b08507"},{"key":"e_1_2_8_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b12075"},{"key":"e_1_2_8_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b01857"},{"key":"e_1_2_8_68_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-020-20872-z"},{"key":"e_1_2_8_69_1","unstructured":"For selected papers on formal hydroacylation reaction of alkenes with other acyl electrophiles with reductants see;"},{"key":"e_1_2_8_70_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200602377"},{"key":"e_1_2_8_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b04937"},{"key":"e_1_2_8_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201900822"},{"key":"e_1_2_8_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c02629"},{"key":"e_1_2_8_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c04970"},{"key":"e_1_2_8_75_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00178a044"},{"key":"e_1_2_8_76_1","unstructured":"See Supporting Information."},{"key":"e_1_2_8_77_1","unstructured":"\u00a0"},{"key":"e_1_2_8_78_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b02204"},{"key":"e_1_2_8_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b08933"},{"key":"e_1_2_8_80_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201900956"},{"key":"e_1_2_8_81_1","doi-asserted-by":"crossref","unstructured":"In the reactions with electron-rich aromatic aldehydes and aliphatic aldehydes additional proton sources such as 2-propanol and acetic acid were added to facilitate the formation of Breslow intermediate. The related reference see; M. Pareek Y. Reddi R.\u2005B. Sunoj Chem. Sci.2021 12 7973\u20137992.","DOI":"10.1039\/D1SC01910D"},{"key":"e_1_2_8_82_1","unstructured":"In most of cases the unreacted aldehydes were recovered. For 1k the benzoin product was obtained."},{"key":"e_1_2_8_83_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3765(19991001)5:10<2810::AID-CHEM2810>3.0.CO;2-F"},{"key":"e_1_2_8_84_1","unstructured":"\u00a0"},{"key":"e_1_2_8_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.6b00251"},{"key":"e_1_2_8_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00205a014"},{"key":"e_1_2_8_87_1","unstructured":"In the reactions with a deuterated aldehyde or reagents the reaction yields were totally low. Although D incorporation was not high these results implied that all these species would act as proton sources in this reaction."},{"key":"e_1_2_8_88_1","unstructured":"\u00a0"},{"key":"e_1_2_8_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00053a031"},{"key":"e_1_2_8_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00041a040"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202301484","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T13:07:56Z","timestamp":1760274476000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202301484"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,7,17]]},"references-count":90,"journal-issue":{"issue":"46","published-print":{"date-parts":[[2023,8,15]]}},"alternative-id":["10.1002\/chem.202301484"],"URL":"https:\/\/doi.org\/10.1002\/chem.202301484","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,7,17]]},"assertion":[{"value":"2023-05-11","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-07-17","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202301484"}}