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The isocyanide double insertion products represent a novel type of 1,2\u2010diimine with a benzoborole backbone. The reduction chemistry of the benzoborole\u2010supported 1,2\u2010diimine was investigated. Single\u2010 and two\u2010electron reduction allow for the isolation and full characterization of a radical anion and a dianion, respectively. In stark contrast to the ordinary boroles, which should turn aromatic by accepting two electrons, the antiaromatic character of the benzoborole backbone is highlighted upon reduction, thus presenting a rare example of antiaromatic borole dianion. Detailed quantum chemical calculations provide a rationale for the observed regioselectivity and the electronic structure of the reduced borole diimine species.<\/jats:p>","DOI":"10.1002\/anie.202312608","type":"journal-article","created":{"date-parts":[[2023,9,27]],"date-time":"2023-09-27T22:59:53Z","timestamp":1695855593000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["A Journey from Benzoborirene to Benzoborole\u2010Supported 1,2\u2010Diimine and Antiaromatic Borolediide"],"prefix":"10.1002","volume":"62","author":[{"given":"Xiaocui","family":"Liu","sequence":"first","affiliation":[{"name":"State Key Laboratory of Traditional Chinese Medicine Syndromes The Second Affiliated Hospital of Guangzhou University of Chinese Medicine  510000 Guangzhou P. R. China"},{"name":"Department of Chemistry Southern University of Science and Technology  518055 Shenzhen P. R. 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