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Biocatalytic oxyfunctionalization reactions of these compounds to the corresponding ketones\/aldehydes are typically hindered by selectivity issues. To address these challenges, the catalytic performance of oxidoreductases is explored. The results show that combining the peroxygenase\u2010catalyzed propargylic C\u2500H bond oxidation with the Old Yellow Enzyme\u2010catalyzed reduction of conjugated C\u2500C triple bonds in one\u2010pot enables the regio\u2010 and chemoselective oxyfunctionalization of sp<jats:sup>3<\/jats:sup> C\u2500H bonds that are distant from benzylic sites. This enzymatic approach yielded a variety of \u03b3\u2010keto arenes with diverse structural and electronic properties in yields of up to 99% and regioselectivity of 100%, which are difficult to achieve using other chemocatalysis and enzymes. By adjusting the C\u2500C triple bond, the carbonyl group's position can be further tuned to yield \u03b5\u2010keto arenes. This enzymatic approach can be combined with other biocatalysts to establish new synthetic pathways for accessing various challenging divergent C\u2500H bond functionalization reactions.<\/jats:p>","DOI":"10.1002\/advs.202304605","type":"journal-article","created":{"date-parts":[[2023,10,23]],"date-time":"2023-10-23T07:25:54Z","timestamp":1698045954000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["A Simple Access to \u03b3\u2010 and \u03b5\u2010Keto Arenes via Enzymatic Divergent C\u2500H Bond Oxyfunctionalization"],"prefix":"10.1002","volume":"10","author":[{"given":"Huanhuan","family":"Li","sequence":"first","affiliation":[{"name":"School of Chemical Engineering and Technology Xi'an Jiaotong University  Xi'an 710049 China"},{"name":"Key Laboratory of Engineering Biology for Low\u2010carbon Manufacturing Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences  32 West 7th Avenue Tianjin 300308 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yalan","family":"Zhang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Engineering Biology for Low\u2010carbon Manufacturing Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences  32 West 7th Avenue Tianjin 300308 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yawen","family":"Huang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Engineering Biology for Low\u2010carbon Manufacturing Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences  32 West 7th Avenue Tianjin 300308 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peigao","family":"Duan","sequence":"additional","affiliation":[{"name":"School of Chemical Engineering and Technology Xi'an Jiaotong University  Xi'an 710049 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ran","family":"Ge","sequence":"additional","affiliation":[{"name":"Key Laboratory of Engineering Biology for Low\u2010carbon Manufacturing Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences  32 West 7th Avenue Tianjin 300308 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaofeng","family":"Han","sequence":"additional","affiliation":[{"name":"Key Laboratory of Engineering Biology for Low\u2010carbon Manufacturing Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences  32 West 7th Avenue Tianjin 300308 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3182-5107","authenticated-orcid":false,"given":"Wuyuan","family":"Zhang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Engineering Biology for Low\u2010carbon Manufacturing Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences  32 West 7th Avenue Tianjin 300308 China"},{"name":"National Innovation Center for Synthetic Biotechnology  32 West 7th Avenue Tianjin 300308 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,10,23]]},"reference":[{"key":"e_1_2_9_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00664"},{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00064B"},{"key":"e_1_2_9_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00583"},{"key":"e_1_2_9_2_3","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs35096c"},{"key":"e_1_2_9_2_4","doi-asserted-by":"publisher","DOI":"10.1021\/cr300153j"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00657"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.6b00546"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41570-021-00300-6"},{"key":"e_1_2_9_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00220"},{"key":"e_1_2_9_6_1","first-page":"2011","volume":"40","author":"Lewis J. 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