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Chem."],"accepted":{"date-parts":[[2021,10,19]]},"abstract":"<jats:p>Reactions of 3-arylpropynenitriles (ArC\u2261CCN) with electron-rich arenes (Ar\u2032H, benzene and its polymethylated derivatives) under the action of aluminum bromide (AlBr<jats:sub>3<\/jats:sub>, 6 equiv) at room temperature for 0.5\u20132 h result in the stereoselective formation of 3,3-diarylpropenenitriles (Ar(Ar\u2032)C=CHCN) in yields of 20\u201364%, as products of mainly <jats:italic>anti-<\/jats:italic>hydroarylation of the acetylene bond. The obtained 3,3-diarylpropenenitriles in triflic acid CF<jats:sub>3<\/jats:sub>SO<jats:sub>3<\/jats:sub>H (TfOH) at room temperature for 1 h are cyclized into 3-arylindenones in yields of 55\u201370%.<\/jats:p>","DOI":"10.3762\/bjoc.17.180","type":"journal-article","created":{"date-parts":[[2021,11,1]],"date-time":"2021-11-01T10:24:35Z","timestamp":1635762275000},"page":"2663-2667","source":"Crossref","is-referenced-by-count":1,"title":["AlBr<sub>3<\/sub>-Promoted stereoselective <i>anti-<\/i>hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles"],"prefix":"10.3762","volume":"17","author":[{"given":"Yelizaveta","family":"Gorbunova","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dmitry S","family":"Ryabukhin","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3628-1492","authenticated-orcid":false,"given":"Aleksander V","family":"Vasilyev","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"2086","published-online":{"date-parts":[[2021,11,1]]},"reference":[{"key":"ref1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2017.07.104"},{"key":"ref2","doi-asserted-by":"publisher","DOI":"10.1016\/s0040-4039(01)81730-5"},{"key":"ref3","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.16.1351"},{"key":"ref4","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob25969a"},{"key":"ref5","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2013.06.095"},{"key":"ref6","doi-asserted-by":"publisher","DOI":"10.1016\/s0040-4020(01)89177-8"},{"key":"ref7","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1610708"},{"key":"ref8","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b00424"},{"key":"ref9","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570430321"},{"key":"ref10","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2011.12.035"},{"key":"ref11","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2018.01.042"},{"key":"ref12","doi-asserted-by":"publisher","DOI":"10.1021\/ja407373g"},{"key":"ref13","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201003572"},{"key":"ref14","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200901484"},{"key":"ref15","doi-asserted-by":"publisher","DOI":"10.1021\/ol006499j"},{"key":"ref16","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2019.02.047"},{"key":"ref17","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2020.131264"},{"key":"ref18","doi-asserted-by":"publisher","DOI":"10.1070\/rc2013v082n03abeh004345"},{"key":"ref19","doi-asserted-by":"publisher","DOI":"10.1134\/s1070428017040017"},{"key":"ref20","doi-asserted-by":"publisher","DOI":"10.2174\/9781681085647118080005"},{"volume-title":"Superlectrophiles and their chemistry","year":"2008","author":"Olah","key":"ref21"},{"key":"ref22","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob06841a"},{"key":"ref23","doi-asserted-by":"publisher","DOI":"10.1055\/s-2002-33918"},{"key":"ref24","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200900067"},{"key":"ref25","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200901262"},{"key":"ref26","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(200009)2000:18<3195::aid-ejoc3195>3.0.co;2-1"},{"key":"ref27","doi-asserted-by":"publisher","DOI":"10.1111\/cbdd.13839"},{"key":"ref28","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202103465"},{"key":"ref29","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201901309"},{"key":"ref30","doi-asserted-by":"publisher","DOI":"10.1016\/j.cclet.2019.03.034"},{"key":"ref31","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201800591"},{"key":"ref32","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2014.09.006"}],"container-title":["Beilstein Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/articles\/17\/180","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/content\/pdf\/1860-5397-17-180.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/articles\/17\/180","content-type":"text\/html","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,11,1]],"date-time":"2021-11-01T10:24:39Z","timestamp":1635762279000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/articles\/17\/180"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,11,1]]},"references-count":32,"URL":"https:\/\/doi.org\/10.3762\/bjoc.17.180","archive":["Portico"],"relation":{},"ISSN":["1860-5397"],"issn-type":[{"type":"electronic","value":"1860-5397"}],"subject":[],"published":{"date-parts":[[2021,11,1]]}}}