{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,21]],"date-time":"2025-11-21T12:24:15Z","timestamp":1763727855807,"version":"build-2065373602"},"reference-count":59,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2020,12,29]],"date-time":"2020-12-29T00:00:00Z","timestamp":1609200000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2021,2,24]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>(<jats:italic>o<\/jats:italic>\u2010Phenylenediamino)borylstannanes were newly synthesized to achieve radical boryl substitutions of a variety of alkyl radical precursors. Dehalogenative, deaminative, decharcogenative, and decarboxylative borylations proceeded in the presence of a radical initiator to give the corresponding organic boron compounds. Radical clock experiments and computational studies have provided insights into the mechanism of the homolytic substitution (S<jats:sub>H<\/jats:sub>2) of the borylstannanes with alkyl radical intermediates. DFT calculation disclosed that the phenylenediamino structure lowered the LUMO level including the vacant p\u2010orbital on the boron atom to enhance the reactivity to alkyl radicals in S<jats:sub>H<\/jats:sub>2. Moreover, C(sp<jats:sup>3<\/jats:sup>)\u2010H borylation of THF was accomplished using the triplet state of xanthone.<\/jats:p>","DOI":"10.1002\/chem.202004692","type":"journal-article","created":{"date-parts":[[2020,11,18]],"date-time":"2020-11-18T04:00:42Z","timestamp":1605672042000},"page":"3968-3973","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["(<i>o<\/i>\u2010Phenylenediamino)borylstannanes: Efficient Reagents for Borylation of Various Alkyl Radical Precursors"],"prefix":"10.1002","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9513-464X","authenticated-orcid":false,"given":"Kensuke","family":"Suzuki","sequence":"first","affiliation":[{"name":"Department of Applied Chemistry Graduate School of Engineering Osaka University, 2-1  Yamadaoka Suita Osaka 565-0871 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However the isolated yield was decreased during the purification by silica gel column chromatography."},{"key":"e_1_2_2_44_1","unstructured":"The generation of the radical would be very slow and the isocyanide2\u2009nis decomposed under heating conditions. Thus the yield of3\u2009nwas low. In fact isocyanide2\u2009nwas not recovered and the complicated by-products were observed."},{"key":"e_1_2_2_45_1","unstructured":"When 2-phenylethyl phenyl sulfide was employed as a radical precursor the yield of the desired product was very low (11\u2009% yield). The simple alkyl radicals are hardly generated from alkylsulfides because C\u2212S bonds are stronger than C\u2212Cl bonds. 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