{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T16:58:36Z","timestamp":1790787516485,"version":"4.1.0"},"reference-count":90,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2024,11,28]],"date-time":"2024-11-28T00:00:00Z","timestamp":1732752000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2024,11,28]],"date-time":"2024-11-28T00:00:00Z","timestamp":1732752000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2025,1,10]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Herein, a copper(I)\u2010catalyzed asymmetric 1,4\u2010hydroarsination of \u03b2\u2010substituted \u03b1,\u03b2\u2010unsaturated esters is achieved in moderate to excellent yields with high to excellent enantioselectivity, based on the proposed nucleophilic [Cu]\u2212AsPh\n                    <jats:sub>2<\/jats:sub>\n                    species. As for \u03b1\u2010substituted \u03b1,\u03b2\u2010unsaturated esters, a 1,4\u2010hydroarsination\/enantioselective protonation event occurs smoothly in satisfying results. Furthermore, \u03b2\u2010substituted \u03b1,\u03b2\u2010unsaturated ketone, \u03b1,\u03b2\u2010unsaturated amide, and \u03b1,\u03b2\u2010unsaturated phosphine sulfide are well applied in the present catalytic system. Finally, some control experiments show that HAsPh\n                    <jats:sub>2<\/jats:sub>\n                    is activated through coordination with the copper(I) catalyst and HAsPh\n                    <jats:sub>2<\/jats:sub>\n                    exhibits inferior soft Lewis basicity to HPPh\n                    <jats:sub>2<\/jats:sub>\n                    in the presence of a copper(I)\u2010bisphosphine complex.\n                  <\/jats:p>","DOI":"10.1002\/anie.202413834","type":"journal-article","created":{"date-parts":[[2024,11,18]],"date-time":"2024-11-18T09:54:24Z","timestamp":1731923664000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Copper(I)\u2010Catalyzed Asymmetric 1,4\u2010Hydroarsination of \u03b1,\u03b2\u2010Unsaturated Compounds"],"prefix":"10.1002","volume":"64","author":[{"given":"Jun\u2010Zhao","family":"Xiao","sequence":"first","affiliation":[{"name":"Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences  345 Lingling Road 200032 Shanghai China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhen\u2010Xi","family":"Cai","sequence":"additional","affiliation":[{"name":"Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences  345 Lingling Road 200032 Shanghai China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhi\u2010Zhou","family":"Pan","sequence":"additional","affiliation":[{"name":"Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences  345 Lingling Road 200032 Shanghai China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ye","family":"Wang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences  345 Lingling Road 200032 Shanghai China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nan","family":"Jiang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences  345 Lingling Road 200032 Shanghai China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9604-5198","authenticated-orcid":false,"given":"Liang","family":"Yin","sequence":"additional","affiliation":[{"name":"Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences  345 Lingling Road 200032 Shanghai China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,11,28]]},"reference":[{"key":"e_1_2_3_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527635207"},{"key":"e_1_2_3_2_1","unstructured":"\u00a0"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020049i"},{"key":"e_1_2_3_4_2","volume-title":"Phosphorus Ligands in Asymmetric Catalysis","author":"Borner 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B."},{"key":"e_1_2_3_25_1","unstructured":"\u00a0"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)00645-X"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)00041-0"},{"key":"e_1_2_3_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/b401585a"},{"key":"e_1_2_3_29_1","unstructured":"\u00a0"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja005875s"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2005.08.003"},{"key":"e_1_2_3_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/om400144s"},{"key":"e_1_2_3_33_1","unstructured":"For some introductions see:"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1999-2528"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.2174\/1385272822666181026120728"},{"key":"e_1_2_3_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2012.06.033"},{"key":"e_1_2_3_37_1","unstructured":"For the syntheses of chiral arsanes rely on direct arsination and\/or depend heavily on classical optical resolution see:"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/om8006272"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic900797y"},{"key":"e_1_2_3_40_1","unstructured":"For some selected reviews see:"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1039\/C1CS15247E"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2014.01.006"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201500220"},{"key":"e_1_2_3_44_2","doi-asserted-by":"publisher","DOI":"10.6023\/cjoc201602018"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0035-1560556"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00692"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1DT03134A"},{"key":"e_1_2_3_48_2","first-page":"14","author":"Novas B. 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Therefore the quenching with S8was employed for the easy separation with column chromatography. It was noted that the sulfidation of tertiary arsanes was much less slow than the corresponding tertiary phosphines. The sulfidation of tertiary phosphines usually finished in 5\u201310\u2005min. However it took more than 8\u2005h to accomplish the sulfidation of tertiary arsanes (3)."},{"key":"e_1_2_3_77_1","unstructured":"The copper-catalyzed asymmetric conjugate hydrophosphinations of both2\u2009raand2\u2009taafforded nearly racemic products under the reaction conditions shown below Y. Wang Z.-Q. Wang L. Yin Synthesis2023 55 2228\u20132240. It was deduced that the produced phosphines in the reactions of2\u2009raand2\u2009taworked as highly competitive chelating ligands to copper(I) which led to the decomposition of Cu+-(R RP)-TANIAPHOS catalyst. Moreover these phosphines were not good ligands in terms of asymmetric induction and thus resulted in nearly racemic products. However 3\u2009raand3\u2009tawere not suitable chelating ligands to copper(I) largely due to the bigger size of As atom than P atom."},{"key":"e_1_2_3_78_1","unstructured":"Deposition number CCDC2270881 (for3\u2009ja) contains the supplementary crystallographic data for this paper. The data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service."},{"key":"e_1_2_3_79_1","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.12.116"},{"key":"e_1_2_3_80_1","unstructured":"For some selected recent examples on the catalytic conjugate addition\/enantioselective protonation reactions see:"},{"key":"e_1_2_3_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b08775"},{"key":"e_1_2_3_82_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b01575"},{"key":"e_1_2_3_83_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201806956"},{"key":"e_1_2_3_84_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202012492"},{"key":"e_1_2_3_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c01073"},{"key":"e_1_2_3_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c03732"},{"key":"e_1_2_3_87_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202300537"},{"key":"e_1_2_3_88_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202301422"},{"key":"e_1_2_3_89_1","unstructured":"Deposition number CCDC2354190 (for7\u2009aa) contains the supplementary crystallographic data for this paper. The data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service."},{"key":"e_1_2_3_90_1","unstructured":"The hydroarsination with \u03b2-phenyl \u03b1 \u03b2-unsaturated diphenylphosphine oxide did not proceed at all at the present catalytic system."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202413834","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202413834","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202413834","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T16:05:20Z","timestamp":1790784320000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202413834"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,11,28]]},"references-count":90,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2025,1,10]]}},"alternative-id":["10.1002\/anie.202413834"],"URL":"https:\/\/doi.org\/10.1002\/anie.202413834","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,11,28]]},"assertion":[{"value":"2024-07-22","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-11-28","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202413834"}}