{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,30]],"date-time":"2026-06-30T19:05:16Z","timestamp":1782846316610,"version":"3.54.5"},"reference-count":127,"publisher":"Wiley","issue":"35","license":[{"start":{"date-parts":[[2021,7,20]],"date-time":"2021-07-20T00:00:00Z","timestamp":1626739200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["R35GM133438"],"award-info":[{"award-number":["R35GM133438"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2021,8,23]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We disclose a nickel\u2010catalyzed reaction, which enabled us to difunctionalize unactivated \u03b3,\u03b4\u2010alkenes in ketones with alkenyl triflates and arylboronic esters. The reaction was made feasible by the use of 5\u2010chloro\u20108\u2010hydroxyquinoline as a ligand along with NiBr<jats:sub>2<\/jats:sub>\u22c5DME as a catalyst and LiO<jats:italic>t<\/jats:italic>Bu as base. The reaction proceeded with a wide range of cyclic, acyclic, endocyclic and exocyclic alkenyl ketones, and electron\u2010rich and electron\u2010deficient arylboronate esters. The reaction also worked with both cyclic and acyclic alkenyl triflates. Control experiments indicate that carbonyl coordination is required for the reaction to proceed.<\/jats:p>","DOI":"10.1002\/anie.202104871","type":"journal-article","created":{"date-parts":[[2021,6,11]],"date-time":"2021-06-11T20:09:41Z","timestamp":1623442181000},"page":"19092-19096","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":34,"title":["Nickel\u2010Catalyzed Regioselective Alkenylarylation of \u03b3,\u03b4\u2010Alkenyl Ketones via Carbonyl Coordination"],"prefix":"10.1002","volume":"60","author":[{"given":"Roshan K.","family":"Dhungana","sequence":"first","affiliation":[{"name":"Department of Chemistry Pennsylvania State University  University Park PA 16802 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vivek","family":"Aryal","sequence":"additional","affiliation":[{"name":"Department of Chemistry Pennsylvania State University  University Park PA 16802 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Doleshwar","family":"Niroula","sequence":"additional","affiliation":[{"name":"Department of Chemistry Pennsylvania State University  University Park PA 16802 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rishi R.","family":"Sapkota","sequence":"additional","affiliation":[{"name":"Department of Chemistry Pennsylvania State University  University Park PA 16802 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Margaret G.","family":"Lakomy","sequence":"additional","affiliation":[{"name":"Department of Chemistry Pennsylvania State University  University Park PA 16802 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8993-9131","authenticated-orcid":false,"given":"Ramesh","family":"Giri","sequence":"additional","affiliation":[{"name":"Department of Chemistry Pennsylvania State University  University Park PA 16802 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,7,20]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"For reviews see:"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201700098"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b03128"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC06006E"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2020.05.013"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0039-1690842"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c02115"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0781846"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar990095d"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0NP00003E"},{"key":"e_1_2_2_11_1","unstructured":"\u00a0"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b02072"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0028-1087339"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201813148"},{"key":"e_1_2_2_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201813148"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b00774"},{"key":"e_1_2_2_16_1","unstructured":"\u00a0"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aaf6123"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aad6080"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja983066r"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol303003g"},{"key":"e_1_2_2_21_1","unstructured":"For selected examples on three-component alkene dicarbofunctionalization see:"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b03163"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b03574"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b04142"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja201358b"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja304344h"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b06917"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c03239"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c00898"},{"key":"e_1_2_2_30_1","unstructured":"\u00a0"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.6b00532"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/om061105z"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.7b00922"},{"key":"e_1_2_2_34_1","unstructured":"For alkene dicarbofunctionalization by cyclization\/coupling see:"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)80814-X"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00659-1"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(97)00754-0"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)01811-1"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2012.02.096"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b12554"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201901067"},{"key":"e_1_2_2_41_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201901067"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b08190"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201913367"},{"key":"e_1_2_2_43_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201913367"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.0c00297"},{"key":"e_1_2_2_45_1","unstructured":"\u00a0"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(89)80008-0"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.66.3522"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1987.193"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)81100-5"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1998-6086"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo016212b"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b01620"},{"key":"e_1_2_2_53_1","unstructured":"For examples of alkene dicarbofunctionalization without a coordinating group see:"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b03195"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b05680"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b05374"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC02127J"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201900228"},{"key":"e_1_2_2_58_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201900228"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b08282"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c08532"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201912746"},{"key":"e_1_2_2_61_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201912746"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202004439"},{"key":"e_1_2_2_62_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202004439"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c09008"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b09245"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC07587E"},{"key":"e_1_2_2_66_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC06509H"},{"key":"e_1_2_2_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201908029"},{"key":"e_1_2_2_67_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201908029"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b09909"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b07194"},{"key":"e_1_2_2_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b06608"},{"key":"e_1_2_2_71_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b06340"},{"key":"e_1_2_2_72_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC04351A"},{"key":"e_1_2_2_73_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC03149A"},{"key":"e_1_2_2_74_1","unstructured":"\u00a0"},{"key":"e_1_2_2_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b06567"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c09922"},{"key":"e_1_2_2_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b04285"},{"key":"e_1_2_2_78_1","unstructured":"For radical-related alkene dicarbofunctionalization and related reactions see:"},{"key":"e_1_2_2_79_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202008498"},{"key":"e_1_2_2_79_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202008498"},{"key":"e_1_2_2_80_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201606458"},{"key":"e_1_2_2_80_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201606458"},{"key":"e_1_2_2_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c03210"},{"key":"e_1_2_2_82_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c03857"},{"key":"e_1_2_2_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c08823"},{"key":"e_1_2_2_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b00915"},{"key":"e_1_2_2_85_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202006439"},{"key":"e_1_2_2_85_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202006439"},{"key":"e_1_2_2_86_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201911012"},{"key":"e_1_2_2_86_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201911012"},{"key":"e_1_2_2_87_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201903353"},{"key":"e_1_2_2_87_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201903353"},{"key":"e_1_2_2_88_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201915837"},{"key":"e_1_2_2_88_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201915837"},{"key":"e_1_2_2_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01258"},{"key":"e_1_2_2_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.9b00248"},{"key":"e_1_2_2_91_1","unstructured":"\u00a0"},{"key":"e_1_2_2_92_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2019.12.026"},{"key":"e_1_2_2_93_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC01735B"},{"key":"e_1_2_2_94_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b09401"},{"key":"e_1_2_2_95_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b07687"},{"key":"e_1_2_2_96_1","unstructured":"For dicarbofunctionlization of carboxylates and carboxamides see:"},{"key":"e_1_2_2_97_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-018-05951-6"},{"key":"e_1_2_2_98_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c03708"},{"key":"e_1_2_2_99_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201913062"},{"key":"e_1_2_2_99_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201913062"},{"key":"e_1_2_2_100_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b11942"},{"key":"e_1_2_2_101_1","unstructured":"While our manuscript was under review one example of ketone-directed alkene diarylation reaction appeared in a preprint. See:10.26434\/chemrxiv.14150174.v1."},{"key":"e_1_2_2_102_1","unstructured":"\u00a0"},{"key":"e_1_2_2_103_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.5b00396"},{"key":"e_1_2_2_104_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.fitote.2014.03.026"},{"key":"e_1_2_2_105_1","unstructured":"Quaternarization of \u03b1-C proximal to alkenes suppressed the reaction regardless of presence or absence of \u03b1-H in alkenylketones. Therefore the role of \u03b1-H in the reaction could not be established unambiguously."},{"key":"e_1_2_2_106_1","unstructured":"For mechanisms of Ni-catalyzed alkene difunctionalization reactions see:"},{"key":"e_1_2_2_107_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b10026"},{"key":"e_1_2_2_108_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.0c00032"},{"key":"e_1_2_2_109_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c02355"},{"key":"e_1_2_2_110_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja063334i"},{"key":"e_1_2_2_111_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.5b00057"},{"key":"e_1_2_2_112_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-14016-1"},{"key":"e_1_2_2_113_1","unstructured":"Deposition Number 2059802 (for33)contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures servicewww.ccdc.cam.ac.uk\/structures."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202104871","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202104871","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202104871","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,28]],"date-time":"2023-08-28T16:14:32Z","timestamp":1693239272000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202104871"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,7,20]]},"references-count":127,"journal-issue":{"issue":"35","published-print":{"date-parts":[[2021,8,23]]}},"alternative-id":["10.1002\/anie.202104871"],"URL":"https:\/\/doi.org\/10.1002\/anie.202104871","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,7,20]]},"assertion":[{"value":"2021-04-08","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-07-20","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}