{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:28:26Z","timestamp":1786976906051,"version":"build-2736575974"},"reference-count":66,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2022,1,11]],"date-time":"2022-01-11T00:00:00Z","timestamp":1641859200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100007215","name":"Verband der Chemischen Industrie","doi-asserted-by":"publisher","award":["Liebig Fellowship"],"award-info":[{"award-number":["Liebig Fellowship"]}],"id":[{"id":"10.13039\/100007215","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":[[2022,2,14]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The ability to selectively react one functional group in the presence of another underpins efficient reaction sequences. Despite many designer catalytic systems being reported for hydroboration reactions, which allow introduction of a functional handle for cross\u2010coupling or act as mild method for reducing polar functionality, these platforms rarely deal with more complex systems where multiple potentially reactive sites exist. Here we demonstrate, for the first time, the ability to use light to distinguish between ketones and carboxylic acids in more complex molecules. By taking advantage of different activation modes, a single catalytic system can be used for hydroboration, with the chemoselectivity dictated only by the presence or absence of visible light.<\/jats:p>","DOI":"10.1002\/anie.202114482","type":"journal-article","created":{"date-parts":[[2021,12,14]],"date-time":"2021-12-14T10:10:38Z","timestamp":1639476638000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":26,"title":["Controlling Chemoselectivity of Catalytic Hydroboration with Light"],"prefix":"10.1002","volume":"61","author":[{"given":"Enrico","family":"Bergamaschi","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry RWTH Aachen University  Landoltweg 1 52074 Aachen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Danijela","family":"Lunic","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry RWTH Aachen University  Landoltweg 1 52074 Aachen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liam A.","family":"McLean","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry RWTH Aachen University  Landoltweg 1 52074 Aachen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Melissa","family":"Hohenadel","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry RWTH Aachen University  Landoltweg 1 52074 Aachen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yi\u2010Kai","family":"Chen","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry RWTH Aachen University  Landoltweg 1 52074 Aachen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0776-5674","authenticated-orcid":false,"given":"Christopher J.","family":"Teskey","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry RWTH Aachen University  Landoltweg 1 52074 Aachen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,1,11]]},"reference":[{"key":"e_1_2_3_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201201787"},{"key":"e_1_2_3_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201201787"},{"key":"e_1_2_3_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41570-018-0071-1"},{"key":"e_1_2_3_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00125B"},{"key":"e_1_2_3_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.1c00733"},{"key":"e_1_2_3_5_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-020-00589-8"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9077528"},{"key":"e_1_2_3_5_3","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c11056"},{"key":"e_1_2_3_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-021-00735-w"},{"key":"e_1_2_3_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00096C"},{"key":"e_1_2_3_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202100164"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202100164"},{"key":"e_1_2_3_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202106183"},{"key":"e_1_2_3_8_4","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202106183"},{"key":"e_1_2_3_8_5","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-10441-4"},{"key":"e_1_2_3_8_6","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201602349"},{"key":"e_1_2_3_8_7","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201602349"},{"key":"e_1_2_3_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202105043"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202105043"},{"key":"e_1_2_3_10_1","unstructured":"\u00a0"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms7652"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-020-0452-y"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.6b00913"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.9b00984"},{"key":"e_1_2_3_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC04584H"},{"key":"e_1_2_3_16_1","unstructured":"\u00a0"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201502980"},{"key":"e_1_2_3_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201502980"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201904452"},{"key":"e_1_2_3_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201904452"},{"key":"e_1_2_3_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202009893"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202009893"},{"key":"e_1_2_3_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c05136"},{"key":"e_1_2_3_21_1","unstructured":"\u00a0"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202000410"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc35727e"},{"key":"e_1_2_3_24_1","unstructured":"\u00a0"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CY00807A"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.9b01877"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201901750"},{"key":"e_1_2_3_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b00362"},{"key":"e_1_2_3_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202005749"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202005749"},{"key":"e_1_2_3_29_3","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c05917"},{"key":"e_1_2_3_29_4","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202012164"},{"key":"e_1_2_3_29_5","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202012164"},{"key":"e_1_2_3_29_6","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202101874"},{"key":"e_1_2_3_29_7","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202101874"},{"key":"e_1_2_3_29_8","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202109089"},{"key":"e_1_2_3_29_9","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202109089"},{"key":"e_1_2_3_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b13520"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c06697"},{"key":"e_1_2_3_31_1","unstructured":"\u00a0"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00956a011"},{"key":"e_1_2_3_33_2","unstructured":"Preliminary1H NMR analysis of the reaction provides support for this step: during the initial stage of the reaction the acid proton of the carboxylic acid (\u03b410.7\u2005ppm) disappears and deshielding of the protons at the \u03b1-position of the carboxylic acid is observed (from \u03b4 2.37 to 2.51\u2005ppm). See Supporting Information for further details."},{"key":"e_1_2_3_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacsau.1c00140"},{"key":"e_1_2_3_35_1","unstructured":"Our preliminary investigations suggest the possibility of a more complex mechanistic scenario whereby the carboxylic acid functionality may in fact be protected as a mixed (boron) anhydride under the \u201clight\u201d reaction conditions via a mechanistic scenario consistent with ref.\u2005[23]. Please see section 8 of the Supporting Information for more detail. We thank one of the reviewers for pertinent suggestions for additional experiments."},{"key":"e_1_2_3_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/0304-5102(93)85073-3"},{"key":"e_1_2_3_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b00428"},{"key":"e_1_2_3_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9OB00485H"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.9b00406"},{"key":"e_1_2_3_39_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC04112B"},{"key":"e_1_2_3_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02775"},{"key":"e_1_2_3_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.8b00900"},{"key":"e_1_2_3_42_1","unstructured":"The reasons for this change in selectivity of the dark process are currently unclear and are the subject of further investigations."},{"key":"e_1_2_3_43_1","unstructured":"For other substrates containing a ketone and a terminal alkene see section 6 of the Supporting Information."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202114482","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202114482","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202114482","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,28]],"date-time":"2023-08-28T07:52:06Z","timestamp":1693209126000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202114482"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,1,11]]},"references-count":66,"journal-issue":{"issue":"8","published-print":{"date-parts":[[2022,2,14]]}},"alternative-id":["10.1002\/anie.202114482"],"URL":"https:\/\/doi.org\/10.1002\/anie.202114482","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,1,11]]},"assertion":[{"value":"2021-10-26","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-01-11","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202114482"}}