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Nevertheless, the limited availability of carbene precursors restricts the introduction of only a single heteroatom. In this report, we describe a new approach based on an I\n                    <jats:sup>(III)<\/jats:sup>\n                    \/S\n                    <jats:sup>(VI)<\/jats:sup>\n                    reagent that promotes the cascade insertion of heteroatoms. This is achieved by sequentially generating two \u03b1\u2010heteroatom\u2010substituted metal carbenes in one reaction. We found that this mixed I\n                    <jats:sup>(III)<\/jats:sup>\n                    \/S\n                    <jats:sup>(VI)<\/jats:sup>\n                    ylide reacts efficiently with a transition metal catalyst and an X\u2212H bond (where X=O, N). This transformation leads to the sequential formation of a sulfoxonium\u2010 and an X\u2010substituted Rh\u2010carbenes, enabling further reactions with another Y\u2212H bond. Remarkably, a wide range of symmetrical and unsymmetrical \u03b1,\u03b1\u2010\n                    <jats:italic>O<\/jats:italic>\n                    ,\n                    <jats:italic>O<\/jats:italic>\n                    \u2010, \u03b1,\u03b1\u2010\n                    <jats:italic>O<\/jats:italic>\n                    ,\n                    <jats:italic>N<\/jats:italic>\n                    \u2010, and \u03b1,\u03b1\u2010\n                    <jats:italic>N<\/jats:italic>\n                    ,\n                    <jats:italic>N<\/jats:italic>\n                    \u2010subsituted ketones can be prepared under mild ambient conditions. In addition, we successfully demonstrated other cascades, such as CN\/CN double amidation, C\u2212H\/C\u2212S double insertion, and C\u2212S\/Y\u2212H double insertion (where Y=S, N, O, C). Notably, the latter two cascades enabled the simultaneous installation of three functional groups to the \u03b1\u2010carbon of carbonyl compounds in a single step. These reactions demonstrate the versatility of our approach, allowing for the synthesis of ketones and esters with multiple \u03b1\u2010heteroatoms using a common precursor.\n                  <\/jats:p>","DOI":"10.1002\/anie.202312793","type":"journal-article","created":{"date-parts":[[2023,9,19]],"date-time":"2023-09-19T04:33:08Z","timestamp":1695097988000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":32,"title":["A Carbene Relay Strategy for Cascade Insertion Reactions"],"prefix":"10.1002","volume":"62","author":[{"given":"Li","family":"Li","sequence":"first","affiliation":[{"name":"Department of Chemistry The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon  Hong Kong SAR China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chenggang","family":"Mi","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemo\/Biosensing and Chemometrics College of Chemistry and Chemical Engineering Hunan University  Changsha Hunan 410082 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Guanwang","family":"Huang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemo\/Biosensing and Chemometrics College of Chemistry and Chemical Engineering Hunan University  Changsha Hunan 410082 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Meirong","family":"Huang","sequence":"additional","affiliation":[{"name":"Shenzhen Bay Laboratory  Shenzhen 518132 China"},{"name":"Laboratory of Computational Chemistry and Drug Design State Key Laboratory of Chemical Oncogenomics Peking University Shenzhen Graduate School  Shenzhen 518055 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuyi","family":"Zhu","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province Shantou University  Shantou Guangdong 515063 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shao\u2010Fei","family":"Ni","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province Shantou University  Shantou Guangdong 515063 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhaofeng","family":"Wang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemo\/Biosensing and Chemometrics College of Chemistry and Chemical Engineering Hunan University  Changsha Hunan 410082 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8377-8923","authenticated-orcid":false,"given":"Yong","family":"Huang","sequence":"additional","affiliation":[{"name":"Department of Chemistry The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon  Hong Kong SAR China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,9,27]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2008.05.018"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr900034e"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4DT01943A"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr940066a"},{"key":"e_1_2_7_5_1","unstructured":"Metal Carbenes in Organic Synthesis Springer Berlin Heidelberg 2004."},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CS00895A"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00382"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00121"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.c21-00757"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201800960"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.1c00664"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CS00542K"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202007001"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0cs00217h"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b02428"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar00157a003"},{"key":"e_1_2_7_17_1","first-page":"1","volume-title":"Adv. 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