{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,6]],"date-time":"2026-09-06T17:37:16Z","timestamp":1788716236347,"version":"build-2803163510"},"reference-count":100,"publisher":"Wiley","issue":"52","license":[{"start":{"date-parts":[[2019,11,11]],"date-time":"2019-11-11T00:00:00Z","timestamp":1573430400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004543","name":"China Scholarship Council","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004543","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008769","name":"Julius-Maximilians-Universit\u00e4t W\u00fcrzburg","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100008769","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":[[2019,12,19]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A convenient and efficient one\u2010step synthesis of 1,1,1\u2010triborylalkanes was achieved via sequential dehydrogenative borylation and double hydroborations of terminal alkynes with HBpin (HBpin=pinacolborane) catalyzed by inexpensive and readily available Cu(OAc)<jats:sub>2<\/jats:sub>. This process proceeds under mild conditions, furnishing 1,1,1\u2010tris(boronates) with wide substrate scope, excellent selectivity, and good functional\u2010group tolerance, and is applicable to gram\u2010scale synthesis without loss of yield. The 1,1,1\u2010triborylalkanes can be used in the preparation of \u03b1\u2010vinylboronates and borylated cyclic compounds, which are valuable but previously rare compounds. Different alkyl groups can be introduced stepwise via base\u2010mediated deborylative alkylation to produce racemic tertiary alkyl boronates, which can be readily transformed into useful tertiary alcohols.<\/jats:p>","DOI":"10.1002\/anie.201909376","type":"journal-article","created":{"date-parts":[[2019,9,6]],"date-time":"2019-09-06T13:35:29Z","timestamp":1567776929000},"page":"18923-18927","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":65,"title":["Copper\u2010Catalyzed Triboration: Straightforward, Atom\u2010Economical Synthesis of 1,1,1\u2010Triborylalkanes from Terminal Alkynes and HBpin"],"prefix":"10.1002","volume":"58","author":[{"given":"Xiaocui","family":"Liu","sequence":"first","affiliation":[{"name":"Institute of Inorganic Chemistry and Institute for Sustainable Chemistry &amp; Catalysis with Boron Julius-Maximilians-Universit\u00e4t W\u00fcrzburg  Am Hubland 97074 W\u00fcrzburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenbo","family":"Ming","sequence":"additional","affiliation":[{"name":"Institute of Inorganic Chemistry and Institute for Sustainable Chemistry &amp; Catalysis with Boron Julius-Maximilians-Universit\u00e4t W\u00fcrzburg  Am Hubland 97074 W\u00fcrzburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yixiao","family":"Zhang","sequence":"additional","affiliation":[{"name":"Institute of Inorganic Chemistry and Institute for Sustainable Chemistry &amp; Catalysis with Boron Julius-Maximilians-Universit\u00e4t W\u00fcrzburg  Am Hubland 97074 W\u00fcrzburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1411-7336","authenticated-orcid":false,"given":"Alexandra","family":"Friedrich","sequence":"additional","affiliation":[{"name":"Institute of Inorganic Chemistry and Institute for Sustainable Chemistry &amp; Catalysis with Boron Julius-Maximilians-Universit\u00e4t W\u00fcrzburg  Am Hubland 97074 W\u00fcrzburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9990-0169","authenticated-orcid":false,"given":"Todd B.","family":"Marder","sequence":"additional","affiliation":[{"name":"Institute of Inorganic Chemistry and Institute for Sustainable Chemistry &amp; Catalysis with Boron Julius-Maximilians-Universit\u00e4t W\u00fcrzburg  Am Hubland 97074 W\u00fcrzburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2019,11,11]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","volume-title":"Boronic Acids: Preparation and Applications in Organic Synthesis Medicine and Materials","year":"2011"},{"key":"e_1_2_2_3_2","volume-title":"Synthesis and Applications of Organoboron Compounds Topics in Organometallic Chemistry, Vol.\u200549","year":"2015"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00193"},{"key":"e_1_2_2_5_1","unstructured":"\u00a0"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/om950918c"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.200400426"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201106706"},{"key":"e_1_2_2_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201106706"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol403326z"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja510081r"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201507372"},{"key":"e_1_2_2_11_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201507372"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7GC01161J"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/cjoc.201700416"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b04665"},{"key":"e_1_2_2_15_2","author":"Liu X.","year":"2019","journal-title":"Angew. Chem. Int. Ed."},{"key":"e_1_2_2_15_3","unstructured":"Angew. Chem. 2019"},{"key":"e_1_2_2_16_1","unstructured":"\u00a0"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9500085"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.81.1535"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/med.20155"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900206p"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201101379"},{"key":"e_1_2_2_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201101379"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00338E"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b00981"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC02316E"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201500284"},{"key":"e_1_2_2_26_1","unstructured":"\u00a0"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010601)40:11<2168::AID-ANIE2168>3.0.CO;2-0"},{"key":"e_1_2_2_27_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010601)113:11<2226::AID-ANGE2226>3.0.CO;2-Q"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.2183\/pjab.84.75"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja105176v"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo1003407"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1150"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja505455z"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja500029w"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201407000"},{"key":"e_1_2_2_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201407000"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b03477"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b00480"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201406680"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201603329"},{"key":"e_1_2_2_38_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201603329"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b02918"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2018.04.061"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201701390"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB02978K"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1612076"},{"key":"e_1_2_2_44_1","unstructured":"\u00a0"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)80082-0"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1975-23686"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199513361"},{"key":"e_1_2_2_47_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19951071213"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1023\/A:1019145818515"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-0682(199910)1999:10<1693::AID-EJIC1693>3.0.CO;2-9"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0682(200102)2001:2<373::AID-EJIC373>3.0.CO;2-6"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201601121"},{"key":"e_1_2_2_51_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201601121"},{"key":"e_1_2_2_52_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc42675k"},{"key":"e_1_2_2_53_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b12896"},{"key":"e_1_2_2_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b12249"},{"key":"e_1_2_2_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b11366"},{"key":"e_1_2_2_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b00445"},{"key":"e_1_2_2_57_1","unstructured":"\u00a0"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.10068"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs300320u"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2014.06.026"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7QO00614D"},{"key":"e_1_2_2_62_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(02)01310-4"},{"key":"e_1_2_2_63_1","unstructured":"Cu-catalyzed hydroboration of alkynes:"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201103612"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201402458"},{"key":"e_1_2_2_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b00325"},{"key":"e_1_2_2_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201600039"},{"key":"e_1_2_2_68_1","unstructured":"Cu-catalyzed dehydrogenative borylation of terminal alkynes:"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6SC02668K"},{"key":"e_1_2_2_70_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2016.09.025"},{"key":"e_1_2_2_71_1","unstructured":"\u00a0"},{"key":"e_1_2_2_72_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-1902(71)80169-0"},{"key":"e_1_2_2_73_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.201402234"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.7b00775"},{"key":"e_1_2_2_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.8b00672"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8DT00627J"},{"key":"e_1_2_2_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.9b01041"},{"key":"e_1_2_2_78_1","unstructured":"The exact oxidation state of Cu and indeed the nuclearity of the active catalyst are not clear as Kleeberg has recently shown that dimeric CuIand higher-order Cu-boryl clusters with Cu oxidation states between 0 and 1 are formed from LCu(OR) and diboron(4) reagents.[15]See also Ref.\u2005[2j]."},{"key":"e_1_2_2_79_1","author":"Kuehn L.","year":"2019","journal-title":"Faraday Discuss."},{"key":"e_1_2_2_80_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201608609"},{"key":"e_1_2_2_80_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201608609"},{"key":"e_1_2_2_81_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja710659y"},{"key":"e_1_2_2_82_1","unstructured":"\u00a0"},{"key":"e_1_2_2_83_2","doi-asserted-by":"publisher","DOI":"10.1039\/c4cy00070f"},{"key":"e_1_2_2_84_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2017.03.011"},{"key":"e_1_2_2_85_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp1081966"},{"key":"e_1_2_2_86_1","first-page":"243","volume":"14","author":"Yuma N.","year":"2017","journal-title":"Lett. Org. Chem."},{"key":"e_1_2_2_87_1","unstructured":"\u00a0"},{"key":"e_1_2_2_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol503111h"},{"key":"e_1_2_2_89_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201801679"},{"key":"e_1_2_2_89_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201801679"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201909376","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201909376","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.201909376","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201909376","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,28]],"date-time":"2023-08-28T17:47:22Z","timestamp":1693244842000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201909376"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,11,11]]},"references-count":100,"journal-issue":{"issue":"52","published-print":{"date-parts":[[2019,12,19]]}},"alternative-id":["10.1002\/anie.201909376"],"URL":"https:\/\/doi.org\/10.1002\/anie.201909376","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,11,11]]},"assertion":[{"value":"2019-07-25","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-11-11","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}