{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,10]],"date-time":"2026-10-10T20:02:32Z","timestamp":1791662552137,"version":"4.3.4"},"reference-count":60,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2022,12,14]],"date-time":"2022-12-14T00:00:00Z","timestamp":1670976000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["HA 3218\/11-1"],"award-info":[{"award-number":["HA 3218\/11-1"]}],"id":[{"id":"10.13039\/501100001659","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":[[2023,1,16]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Complex [(<jats:sup>DIPeP<\/jats:sup>BDI)Ca]<jats:sub>2<\/jats:sub>(C<jats:sub>6<\/jats:sub>H<jats:sub>6<\/jats:sub>), with a C<jats:sub>6<\/jats:sub>H<jats:sub>6<\/jats:sub><jats:sup>2\u2212<\/jats:sup>dianion bridging two Ca<jats:sup>2+<\/jats:sup>ions, reacts with benzene to yield [(<jats:sup>DIPeP<\/jats:sup>BDI)Ca]<jats:sub>2<\/jats:sub>(biphenyl) with a bridging biphenyl<jats:sup>2\u2212<\/jats:sup>dianion (<jats:sup>DIPeP<\/jats:sup>BDI=HC[C(Me)N\u2010DIPeP]<jats:sub>2<\/jats:sub>; DIPeP=2,6\u2010CH(Et)<jats:sub>2<\/jats:sub>\u2010phenyl). The biphenyl complex was also prepared by reacting [(<jats:sup>DIPeP<\/jats:sup>BDI)Ca]<jats:sub>2<\/jats:sub>(C<jats:sub>6<\/jats:sub>H<jats:sub>6<\/jats:sub>) with biphenyl or by reduction of [(<jats:sup>DIPeP<\/jats:sup>BDI)CaI]<jats:sub>2<\/jats:sub>with KC<jats:sub>8<\/jats:sub>in presence of biphenyl. Benzene\u2010benzene coupling was also observed when the deep purple product of ball\u2010milling [(<jats:sup>DIPP<\/jats:sup>BDI)CaI(THF)]<jats:sub>2<\/jats:sub>with K\/KI was extracted with benzene (DIPP=2,6\u2010CH(Me)<jats:sub>2<\/jats:sub>\u2010phenyl) giving crystalline [(<jats:sup>DIPP<\/jats:sup>BDI)Ca(THF)]<jats:sub>2<\/jats:sub>(biphenyl) (52\u2009% yield). Reduction of [(<jats:sup>DIPeP<\/jats:sup>BDI)SrI]<jats:sub>2<\/jats:sub>with KC<jats:sub>8<\/jats:sub>gave highly labile [(<jats:sup>DIPeP<\/jats:sup>BDI)Sr]<jats:sub>2<\/jats:sub>(C<jats:sub>6<\/jats:sub>H<jats:sub>6<\/jats:sub>) as a black powder (61\u2009% yield) which reacts rapidly and selectively with benzene to [(<jats:sup>DIPeP<\/jats:sup>BDI)Sr]<jats:sub>2<\/jats:sub>(biphenyl). DFT calculations show that the most likely route for biphenyl formation is a pathway in which the C<jats:sub>6<\/jats:sub>H<jats:sub>6<\/jats:sub><jats:sup>2\u2212<\/jats:sup>dianion attacks neutral benzene. This is facilitated by metal\u2010benzene coordination.<\/jats:p>","DOI":"10.1002\/anie.202212463","type":"journal-article","created":{"date-parts":[[2022,11,25]],"date-time":"2022-11-25T09:20:51Z","timestamp":1669368051000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":40,"title":["Alkaline\u2010Earth Metal Mediated Benzene\u2010to\u2010Biphenyl Coupling"],"prefix":"10.1002","volume":"62","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0766-3918","authenticated-orcid":false,"given":"Jonathan","family":"Mai","sequence":"first","affiliation":[{"name":"Inorganic and Organometallic Chemistry Universit\u00e4t Erlangen-N\u00fcrnberg Egerlandstrasse 1 91058 Erlangen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael","family":"Morasch","sequence":"additional","affiliation":[{"name":"Inorganic and Organometallic Chemistry Universit\u00e4t Erlangen-N\u00fcrnberg Egerlandstrasse 1 91058 Erlangen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6233-6568","authenticated-orcid":false,"given":"Dawid","family":"J\u0119drzkiewicz","sequence":"additional","affiliation":[{"name":"Inorganic and Organometallic Chemistry Universit\u00e4t Erlangen-N\u00fcrnberg Egerlandstrasse 1 91058 Erlangen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2895-4979","authenticated-orcid":false,"given":"Jens","family":"Langer","sequence":"additional","affiliation":[{"name":"Inorganic and Organometallic Chemistry Universit\u00e4t Erlangen-N\u00fcrnberg Egerlandstrasse 1 91058 Erlangen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3756-9842","authenticated-orcid":false,"given":"Bastian","family":"R\u00f6sch","sequence":"additional","affiliation":[{"name":"Inorganic and Organometallic Chemistry Universit\u00e4t Erlangen-N\u00fcrnberg Egerlandstrasse 1 91058 Erlangen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3997-1440","authenticated-orcid":false,"given":"Sjoerd","family":"Harder","sequence":"additional","affiliation":[{"name":"Inorganic and Organometallic Chemistry Universit\u00e4t Erlangen-N\u00fcrnberg Egerlandstrasse 1 91058 Erlangen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,12,14]]},"reference":[{"key":"e_1_2_3_1_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1128684"},{"key":"e_1_2_3_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr000664r"},{"key":"e_1_2_3_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.arabjc.2013.07.035"},{"key":"e_1_2_3_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.19043320104"},{"key":"e_1_2_3_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/cen-v082n036.p049"},{"key":"e_1_2_3_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar020230d"},{"key":"e_1_2_3_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0NJ02230F"},{"key":"e_1_2_3_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2FD00121G"},{"key":"e_1_2_3_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/1615-4169(200107)343:5<455::AID-ADSC455>3.0.CO;2-O"},{"key":"e_1_2_3_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC05510F"},{"key":"e_1_2_3_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201300990"},{"key":"e_1_2_3_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19100430288"},{"key":"e_1_2_3_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201210238"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201210238"},{"key":"e_1_2_3_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201904934"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201904934"},{"key":"e_1_2_3_15_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-016-0435-5"},{"key":"e_1_2_3_16_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1989-27316"},{"key":"e_1_2_3_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100211a013"},{"key":"e_1_2_3_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3976000611B"},{"key":"e_1_2_3_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0379-6779(00)00222-8"},{"key":"e_1_2_3_20_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.abf2374"},{"key":"e_1_2_3_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202200511"},{"key":"e_1_2_3_21_2","doi-asserted-by":"crossref","first-page":"e202200511","DOI":"10.1002\/ange.202200511","volume":"134","year":"2022","journal-title":"Angew. Chem."},{"key":"e_1_2_3_22_1","doi-asserted-by":"crossref","first-page":"e202200138","DOI":"10.1002\/zaac.202200138","author":"J\u0119drzkiewicz D.","year":"2022","journal-title":"Z. Anorg. Allg. Chem."},{"key":"e_1_2_3_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200601013"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200601013"},{"key":"e_1_2_3_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202200305"},{"key":"e_1_2_3_24_2","doi-asserted-by":"crossref","first-page":"e202200305","DOI":"10.1002\/ange.202200305","volume":"134","year":"2022","journal-title":"Angew. Chem."},{"key":"e_1_2_3_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.2c00427"},{"key":"e_1_2_3_26_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0365110X6100334X"},{"key":"e_1_2_3_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC05792J"},{"key":"e_1_2_3_28_1","unstructured":"\u00a0"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5DT02198G"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201412168"},{"key":"e_1_2_3_30_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201412168"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/B715027J"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202100605"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja980377t"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5SC02486B"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201612010"},{"key":"e_1_2_3_35_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201612010"},{"key":"e_1_2_3_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201812051"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201812051"},{"key":"e_1_2_3_37_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1392"},{"key":"e_1_2_3_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2CC04841H"},{"key":"e_1_2_3_39_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aao5923"},{"key":"e_1_2_3_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201901548"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201901548"},{"key":"e_1_2_3_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202017126"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202017126"},{"key":"e_1_2_3_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/om0490334"},{"key":"e_1_2_3_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja005580e"},{"key":"e_1_2_3_44_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.4906944"},{"key":"e_1_2_3_45_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC04083D"},{"key":"e_1_2_3_46_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8DT03124J"},{"key":"e_1_2_3_47_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC04147A"},{"key":"e_1_2_3_48_1","doi-asserted-by":"publisher","DOI":"10.1038\/s42004-020-00408-8"},{"key":"e_1_2_3_49_1","doi-asserted-by":"publisher","DOI":"10.1038\/s44160-022-00077-6"},{"key":"e_1_2_3_50_1","unstructured":"Deposition Numbers2202205 (for1-THF) 2202206 (for2-THF) 2202207 (for2-THP) 2202208 (for3) 2202209 (for4) and 2202210 (for5)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.202212463","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202212463","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202212463","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,12,1]],"date-time":"2023-12-01T19:41:30Z","timestamp":1701459690000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202212463"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,12,14]]},"references-count":60,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2023,1,16]]}},"alternative-id":["10.1002\/anie.202212463"],"URL":"https:\/\/doi.org\/10.1002\/anie.202212463","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,12,14]]},"assertion":[{"value":"2022-08-24","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-12-14","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202212463"}}