{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,20]],"date-time":"2026-05-20T05:14:22Z","timestamp":1779254062515,"version":"3.51.4"},"reference-count":76,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2022,12,20]],"date-time":"2022-12-20T00:00:00Z","timestamp":1671494400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100005156","name":"Alexander von Humboldt-Stiftung","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100005156","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":[[2023,1,23]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Hydroboration of styrene or vinylcyclohexane with the IMes(C<jats:sub>6<\/jats:sub>F<jats:sub>5<\/jats:sub>)BH<jats:sup>+<\/jats:sup> cation followed by deprotonation provided a convenient synthetic entry to the [B]=CHCH<jats:sub>2<\/jats:sub>R boraalkenes <jats:bold>9\u2009a<\/jats:bold> and <jats:bold>9\u2009b<\/jats:bold>. The in situ generated IMes(SCN)BH<jats:sup>+<\/jats:sup> system reacted similarly with 1,1\u2010diphenylethene followed by deprotonation to give the isothiocyanato substituted boraalkene <jats:bold>9\u2009c<\/jats:bold>. The boraalkenes underwent [2+2] cycloaddition reactions with a small series of heterocumulenes to give the respective four\u2010membered heterocycles. The [B]=CHCH<jats:sub>2<\/jats:sub>R+CO<jats:sub>2<\/jats:sub> cycloadducts <jats:bold>13\u2009a<\/jats:bold> and <jats:bold>13\u2009b<\/jats:bold> added the borane HB(C<jats:sub>6<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub> with cleavage of the central B\u2212C \u03c3\u2010bond. CS<jats:sub>2<\/jats:sub> underwent an unusual reaction with the boraalkenes, namely insertion into the B=C bond with formation of the borylated dithioketene acetal under complete rupture of the strong B=C double bond. The intermediate dithiobora\u2010\u03b2\u2010lactone type intermediate was isolated in the case of the isothiocyanato\u2010boraalkene reaction and characterized by X\u2010ray diffraction.<\/jats:p>","DOI":"10.1002\/anie.202214700","type":"journal-article","created":{"date-parts":[[2022,11,26]],"date-time":"2022-11-26T14:51:01Z","timestamp":1669474261000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Boraalkenes Made by a Hydroboration Route: Cycloaddition and B=C Bond Cleavage Reactions"],"prefix":"10.1002","volume":"62","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3333-3082","authenticated-orcid":false,"given":"Xiaoming","family":"Jie","sequence":"first","affiliation":[{"name":"Organisch-Chemisches Institut Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstra\u00dfe 40 48149 M\u00fcnster Germany"},{"name":"State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of Matter Chinese Academy of Sciences  Fuzhou 350002 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2761-3766","authenticated-orcid":false,"given":"Chaohuang","family":"Chen","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstra\u00dfe 40 48149 M\u00fcnster Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Constantin G.","family":"Daniliuc","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstra\u00dfe 40 48149 M\u00fcnster Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5196-2491","authenticated-orcid":false,"given":"Gerald","family":"Kehr","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstra\u00dfe 40 48149 M\u00fcnster Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2488-3699","authenticated-orcid":false,"given":"Gerhard","family":"Erker","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstra\u00dfe 40 48149 M\u00fcnster Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2022,12,20]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"For boraalkene related examples see:"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198813311"},{"key":"e_1_2_7_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19881001012"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198813701"},{"key":"e_1_2_7_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19881001032"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199010301"},{"key":"e_1_2_7_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19901020925"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198504161"},{"key":"e_1_2_7_5_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19850970527"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198308771"},{"key":"e_1_2_7_6_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19830951111"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201412006"},{"key":"e_1_2_7_7_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201412006"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201506368"},{"key":"e_1_2_7_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201506368"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b07823"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201608994"},{"key":"e_1_2_7_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201608994"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202002125"},{"key":"e_1_2_7_11_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202002125"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202100919"},{"key":"e_1_2_7_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202100919"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c09774"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2020.213647"},{"key":"e_1_2_7_15_1","unstructured":"For borataalkene examples see:"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00774a047"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00789a068"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00242a064"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200702299"},{"key":"e_1_2_7_19_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200702299"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC02223C"},{"key":"e_1_2_7_21_1","unstructured":"\u00a0"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202106724"},{"key":"e_1_2_7_22_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202106724"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2DT01193J"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2SC02485C"},{"key":"e_1_2_7_25_1","unstructured":"\u00a0"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202009353"},{"key":"e_1_2_7_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202009353"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr200133c"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200500402"},{"key":"e_1_2_7_28_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200500402"},{"key":"e_1_2_7_29_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197507451"},{"key":"e_1_2_7_30_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19750872104"},{"key":"e_1_2_7_31_2","doi-asserted-by":"crossref","first-page":"299","DOI":"10.1016\/B978-008044992-0.01210-4","volume-title":"Comprehensive Heterocyclic Chemistry III, Vol.\u200513","author":"Haddadin M. J.","year":"2008"},{"key":"e_1_2_7_32_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199720361"},{"key":"e_1_2_7_33_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19971091904"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(97)10427-6"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20000901)39:17<3012::AID-ANIE3012>3.0.CO;2-G"},{"key":"e_1_2_7_35_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20000901)112:17<3140::AID-ANGE3140>3.0.CO;2-G"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c01096"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/om100152v"},{"key":"e_1_2_7_38_1","unstructured":"\u00a0"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja107025y"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja305061c"},{"key":"e_1_2_7_41_1","unstructured":"\u00a0"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01502a063"},{"key":"e_1_2_7_43_2","first-page":"1","volume":"13","author":"Zweifel G.","year":"1963","journal-title":"Org. React."},{"key":"e_1_2_7_44_2","first-page":"877","volume-title":"Comprehensive Organic Synthesis, Vol.\u20058","author":"Zaidlewicz M.","year":"2014"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1139\/v05-240"},{"key":"e_1_2_7_46_1","unstructured":"For reviews see:"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200703883"},{"key":"e_1_2_7_47_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200703883"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature13384"},{"key":"e_1_2_7_49_1","unstructured":"\u00a0"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202015508"},{"key":"e_1_2_7_50_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202015508"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC01580J"},{"key":"e_1_2_7_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol201957n"},{"key":"e_1_2_7_53_1","unstructured":"\u00a0"},{"key":"e_1_2_7_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199508091"},{"key":"e_1_2_7_54_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19951070724"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/om980673e"},{"key":"e_1_2_7_56_1","unstructured":"Deposition numbers\u20052155668 (8\u2009a) 2155669 (8\u2009b) 2155670 (9\u2009a) 2155671 (9\u2009b) 2208243 (9\u2009c) 2208502 (11) 2155672 (12\u2009a) 2155666 (13\u2009a) 2155667 (13\u2009b) 2208245 (13\u2009c) 2155673 (14\u2009a) 2155674 (15\u2009a) 2155675 (16\u2009a) 2155676 (17\u2009a) 2208246 (17\u2009c) 2208247 (18\u2009c) 2155677 (20\u2009a) 2155678 (21\u2009a) and 2155679 (23\u2009b)contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202214700","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202214700","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202214700","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,20]],"date-time":"2023-08-20T08:33:22Z","timestamp":1692520402000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202214700"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,12,20]]},"references-count":76,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2023,1,23]]}},"alternative-id":["10.1002\/anie.202214700"],"URL":"https:\/\/doi.org\/10.1002\/anie.202214700","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,12,20]]},"assertion":[{"value":"2022-10-06","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-12-20","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202214700"}}