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Therefore, synthetic methods that provide access to novel saturated nitrogen\u2010containing heterocycles are in high demand. Herein, we report a general synthesis of 1\u2010azabicyclo[2.1.1]hexanes (1\u2010aza\u2010BCH) via a formal cycloaddition of azabicyclo[1.1.0]butanes (ABB) with styrenes under photochemical conditions. To overcome the challenging direct single electron reduction of ABBs, we designed a polar\u2010radical\u2010polar relay strategy that leverages a fast acid\u2010mediated ring\u2010opening of ABBs to form bromoazetidines, which undergo efficient debrominative radical formation to initiate the cycloaddition reaction. The reaction is applicable to a broad range of ABB\u2010ketones and we demonstrate the 1\u2010aza\u2010BCH products can be further functionalized to access larger saturated, conformationally rigid heterocycles.<\/jats:p>","DOI":"10.1002\/anie.202410207","type":"journal-article","created":{"date-parts":[[2024,7,22]],"date-time":"2024-07-22T19:24:57Z","timestamp":1721676297000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":36,"title":["Synthesis of 1\u2010Azabicyclo[2.1.1]hexanes via Formal Single Electron Reduction of Azabicyclo[1.1.0]butanes under Photochemical Conditions"],"prefix":"10.1002","volume":"63","author":[{"given":"Margherita","family":"Zanini","sequence":"first","affiliation":[{"name":"School of Chemistry University of Bristol  Cantock's Close Bristol BS8 1TS"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Adam","family":"Noble","sequence":"additional","affiliation":[{"name":"School of Chemistry University of Bristol  Cantock's Close Bristol BS8 1TS"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0344-6430","authenticated-orcid":false,"given":"Varinder K.","family":"Aggarwal","sequence":"additional","affiliation":[{"name":"School of Chemistry University of Bristol  Cantock's Close Bristol BS8 1TS"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,9,20]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB02812E"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0MD00370K"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201804225"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.1c01215"},{"key":"e_1_2_3_6_1","unstructured":"\u00a0"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.8b00888"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201510675"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201700082"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm300094u"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.0c00195"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.6b00281"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-023-01222-0"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2008.11.015"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm960254o"},{"key":"e_1_2_3_16_1","unstructured":"\u00a0"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202004183"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202000548"},{"key":"e_1_2_3_19_1","unstructured":"\u00a0"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c01786"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm501100b"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm4017625"},{"key":"e_1_2_3_23_1","unstructured":"\u00a0"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202204719"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.0c00039"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b02071"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(80)80077-3"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(80)80078-5"},{"key":"e_1_2_3_29_1","unstructured":"\u00a0"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39850000686"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200690044"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202114235"},{"key":"e_1_2_3_33_1","unstructured":"\u00a0"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-023-01135-y"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202214507"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.3c00305"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c08206"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202314700"},{"key":"e_1_2_3_39_2","first-page":"24466","volume":"145","author":"Robichon M.","year":"2023","journal-title":"J. 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