{"title":"Reductive Cleavage of C-O and C-N Bonds by Homogeneous Transition-Metal Catalysis","authors":"Yumeng Liao, Kohei Takahashi, Kyoko Nozaki","doi":"10.5059/yukigoseikyokaishi.83.1006","DOIUrl":"https://doi.org/10.5059/yukigoseikyokaishi.83.1006","url":null,"abstract":"The selective cleavage of carbon-oxygen (C-O) and carbon-nitrogen (C-N) bonds remains a fundamental transformation in organic synthesis, offering a versatile platform for constructing new chemical bonds. In particular, homogeneous transition metal catalysis has enabled highly selective reductive cleavage of ethereal C-O bonds under mild conditions, providing new strategies for both small molecule functionalisation and polymer degradation. Meanwhile, recent advances have extended this approach to more challenging C-N bonds. This review highlights recent advances in the development of homogeneous catalysis for the reductive cleavage of C-O and C-N bonds alongside their mechanistic insights. Additionally, emerging applications in the valorisation of polymers such as lignin and epoxy resins highlight the broader impact of reductive cleavage of C-O bonds.","PeriodicalId":17123,"journal":{"name":"Journal of Synthetic Organic Chemistry Japan","volume":"83 11","pages":"1006-1013"},"PeriodicalIF":0.0,"publicationDate":"2025-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/83/11/83_1006/_pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147894427","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of the Reducing End Fuc-Agl Fragment of Saccharomicins","authors":"Dengxian Fu, Shiwei Xu, Lingkui Meng, Qian Wan, Jing Zeng","doi":"10.6023/cjoc202409041","DOIUrl":"https://doi.org/10.6023/cjoc202409041","url":null,"abstract":"","PeriodicalId":17123,"journal":{"name":"Journal of Synthetic Organic Chemistry Japan","volume":"45 3","pages":"945-945"},"PeriodicalIF":0.0,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147915982","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Guiling Xie, Sudhakar Reddy Mopuri, Jie Jack Li, Yuanyong Yang, Tie-Gen Chen
{"title":"One-Pot Transition-Metal-Free Synthesis of Carboline Derivatives via Dual C—N Bond Formation","authors":"Guiling Xie, Sudhakar Reddy Mopuri, Jie Jack Li, Yuanyong Yang, Tie-Gen Chen","doi":"10.6023/cjoc202505007","DOIUrl":"https://doi.org/10.6023/cjoc202505007","url":null,"abstract":"","PeriodicalId":17123,"journal":{"name":"Journal of Synthetic Organic Chemistry Japan","volume":"45 10","pages":"3824-3824"},"PeriodicalIF":0.0,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147919114","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Transition Metal-Free Selective Aerobic Olefination of Methyl <i>N</i>-Heteroarenes with Alcohols","authors":"Jie Liu, Feng Han, Shuangyan Li, Tianyu Chen, Jianhui Chen, Qing Xu","doi":"10.6023/cjoc202308011","DOIUrl":"https://doi.org/10.6023/cjoc202308011","url":null,"abstract":"By performing the reactions in the presence of adequate amount of air and a suitable base, selective olefination of methyl N-heteroarenes with alcohols can be effectively achieved without using any external catalyst. Control experiments revealed that, with adequate air, base can promote the aerobic oxidation of alcohols almost completely to carbonyl intermediates, which then condense with the methyl N-heteroarenes to afford the alkenyl N-heteroarene products. As the reaction is performed with adequate amount of air and a lower loading of the base at a lower temperature than that of the alkylation reaction, the generated alkenyl N-heteroarenes cannot be transfer hydrogenated to the alkylated products by the remained small amount of alcohol in the reaction mixture, which leads to a high selectivity of the olefination reaction. This method is thus a practical way for preparation of the alkenyl N-heteroarenes, being a complementary method to previous transition metal-free C-alkylation reaction of methyl N-heteroarenes with alcohols in the presence of small amount of air.","PeriodicalId":17123,"journal":{"name":"Journal of Synthetic Organic Chemistry Japan","volume":"44 2","pages":"573-573"},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"http://sioc-journal.cn/Jwk_yjhx/EN/article/downloadArticleFile.do?attachType=PDF&id=350488","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147895618","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}