{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T02:39:17Z","timestamp":1791945557237,"version":"4.3.4"},"reference-count":60,"publisher":"American Association for the Advancement of Science (AAAS)","issue":"6716","content-domain":{"domain":["www.science.org"],"crossmark-restriction":true},"short-container-title":["Science"],"published-print":{"date-parts":[[2024,9,27]]},"abstract":"<jats:p>The excitation of carbonyl compounds by light to generate radical intermediates has historically been restricted to ketones and aldehydes; carboxylic acids have been overlooked because of high energy requirements and low quantum efficiency. A successful activation strategy would necessitate a bathochromic shift in the absorbance profile, an increase in triplet diradical lifetime, and ease of further functionalization. We present a single-flask transformation of carboxylic acids to acyl phosphonates that can access synthetically useful triplet diradicals under visible light or near-ultraviolet irradiation. The use of phosphorus circumvents unproductive Norrish type I processes, promoting selectivity that enables hydrogen-atom transfer reactivity. Use of this strategy promotes the efficient scaffold remodeling of carboxylic acids through various annulation, contraction, and expansion manifolds.<\/jats:p>","DOI":"10.1126\/science.adr0771","type":"journal-article","created":{"date-parts":[[2024,9,26]],"date-time":"2024-09-26T18:00:52Z","timestamp":1727373652000},"page":"1471-1477","update-policy":"https:\/\/doi.org\/10.34133\/aaas_crossmark","source":"Crossref","is-referenced-by-count":37,"title":["Photochemical phosphorus-enabled scaffold remodeling of carboxylic acids"],"prefix":"10.1126","volume":"385","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5501-3947","authenticated-orcid":true,"given":"Qiupeng","family":"Peng","sequence":"first","affiliation":[{"name":"Department of Chemistry, Northwestern University, Evanston, IL 60208, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0008-4520-8389","authenticated-orcid":true,"given":"Meemie U.","family":"Hwang","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Northwestern University, Evanston, IL 60208, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9411-8805","authenticated-orcid":true,"given":"\u00c1ngel","family":"Renter\u00eda-G\u00f3mez","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Texas A&amp;M University, College Station, TX 77843, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2876-7612","authenticated-orcid":true,"given":"Poulami","family":"Mukherjee","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Texas A&amp;M University, College Station, TX 77843, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5108-0261","authenticated-orcid":true,"given":"Ryan M.","family":"Young","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Northwestern University, Evanston, IL 60208, USA."},{"name":"Paula M. Trienens Institute for Sustainability and Energy, Northwestern University, Evanston, IL 60208, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4666-1424","authenticated-orcid":true,"given":"Yunfan","family":"Qiu","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Northwestern University, Evanston, IL 60208, USA."},{"name":"Paula M. Trienens Institute for Sustainability and Energy, Northwestern University, Evanston, IL 60208, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2920-5440","authenticated-orcid":true,"given":"Michael R.","family":"Wasielewski","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Northwestern University, Evanston, IL 60208, USA."},{"name":"Paula M. Trienens Institute for Sustainability and Energy, Northwestern University, Evanston, IL 60208, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8151-7519","authenticated-orcid":true,"given":"Osvaldo","family":"Gutierrez","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Texas A&amp;M University, College Station, TX 77843, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4856-3569","authenticated-orcid":true,"given":"Karl A.","family":"Scheidt","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Northwestern University, Evanston, IL 60208, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"221","reference":[{"key":"e_1_3_2_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300503r"},{"key":"e_1_3_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00662"},{"key":"e_1_3_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00057"},{"key":"e_1_3_2_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201709766"},{"key":"e_1_3_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00993"},{"key":"e_1_3_2_7_2","doi-asserted-by":"publisher","DOI":"10.1038\/140195b0"},{"key":"e_1_3_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01544a092"},{"key":"e_1_3_2_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/cs9720100465"},{"key":"e_1_3_2_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200907155"},{"key":"e_1_3_2_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202217210"},{"key":"e_1_3_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0680336"},{"key":"e_1_3_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201002845"},{"key":"e_1_3_2_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/B913880N"},{"key":"e_1_3_2_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB01214K"},{"key":"e_1_3_2_16_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.abi7183"},{"key":"e_1_3_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00789a067"},{"key":"e_1_3_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201804006"},{"key":"e_1_3_2_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CS00054A"},{"key":"e_1_3_2_20_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-022-04636-x"},{"key":"e_1_3_2_21_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1244809"},{"key":"e_1_3_2_22_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aai8228"},{"key":"e_1_3_2_23_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1255525"},{"key":"e_1_3_2_24_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature22307"},{"key":"e_1_3_2_25_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aan3679"},{"key":"e_1_3_2_26_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-022-05211-0"},{"key":"e_1_3_2_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030451c"},{"key":"e_1_3_2_28_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aam7936"},{"key":"e_1_3_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c06524"},{"key":"e_1_3_2_30_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2023.03.016"},{"key":"e_1_3_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c00557"},{"key":"e_1_3_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.6b01437"},{"key":"e_1_3_2_33_2","doi-asserted-by":"publisher","DOI":"10.1038\/s44160-022-00052-1"},{"key":"e_1_3_2_34_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.42.821"},{"key":"e_1_3_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar50153a004"},{"key":"e_1_3_2_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja990896b"},{"key":"e_1_3_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm0701627"},{"key":"e_1_3_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0485971"},{"key":"e_1_3_2_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201800598"},{"key":"e_1_3_2_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp075829f"},{"key":"e_1_3_2_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp409883a"},{"key":"e_1_3_2_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201504576"},{"key":"e_1_3_2_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00123a018"},{"key":"e_1_3_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja982463z"},{"key":"e_1_3_2_45_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2023.04.011"},{"key":"e_1_3_2_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol103119u"},{"key":"e_1_3_2_47_2","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevB.37.785"},{"key":"e_1_3_2_48_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.464913"},{"key":"e_1_3_2_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.20078"},{"key":"e_1_3_2_50_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.3382344"},{"key":"e_1_3_2_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.30"},{"key":"e_1_3_2_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar3000844"},{"key":"e_1_3_2_53_2","doi-asserted-by":"publisher","DOI":"10.1039\/b508541a"},{"key":"e_1_3_2_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/b515623h"},{"key":"e_1_3_2_55_2","doi-asserted-by":"publisher","DOI":"10.1039\/P29930000799"},{"key":"e_1_3_2_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00031a013"},{"key":"e_1_3_2_57_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.469990"},{"key":"e_1_3_2_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp9716997"},{"key":"e_1_3_2_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.10189"},{"key":"e_1_3_2_60_2","unstructured":"M. J. Frisch et al. Gaussian 16 revision C.01 (Gaussian Inc. 2019)."},{"key":"e_1_3_2_61_2","unstructured":"C. Y. Legault CYLview20 (Universit\u00e9 de Sherbrooke 2020); www.cylview.org."}],"container-title":["Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.science.org\/doi\/pdf\/10.1126\/science.adr0771","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,9,26]],"date-time":"2024-09-26T18:01:01Z","timestamp":1727373661000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.science.org\/doi\/10.1126\/science.adr0771"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,9,27]]},"references-count":60,"journal-issue":{"issue":"6716","published-print":{"date-parts":[[2024,9,27]]}},"alternative-id":["10.1126\/science.adr0771"],"URL":"https:\/\/doi.org\/10.1126\/science.adr0771","relation":{},"ISSN":["0036-8075","1095-9203"],"issn-type":[{"value":"0036-8075","type":"print"},{"value":"1095-9203","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,9,27]]},"assertion":[{"value":"2024-06-13","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-08-27","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-09-26","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}