Ben Stokes, Xiaofeng Cai, Ritter V. Amsbaugh, Lauren J. Drake, Ravi M. A. Kotamraju, Nicholas Javier C. Licauco
{"title":"叔丁氧羰基介导的 α-季均苯甲醛原醛脱羰基反应","authors":"Ben Stokes, Xiaofeng Cai, Ritter V. Amsbaugh, Lauren J. Drake, Ravi M. A. Kotamraju, Nicholas Javier C. Licauco","doi":"10.1055/a-2231-3108","DOIUrl":null,"url":null,"abstract":"\n Tert-butoxide mediates the Haller–Bauer-type (protodeformylative) decarbonylation of readily accessed α-quaternary homobenzaldehydes and related compounds at room temperature, generating cumene products. Both geminal dialkyl and geminal diaryl substituents are tolerated. Gem-dimethyls are sufficient for decarbonylation of polycyclic arenyl substrates whereas monocyclic aromatic homobenzaldehydes require cyclic gem-dialkyls or gem-diaryls for significant decarbonylation.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" 38","pages":""},"PeriodicalIF":2.0000,"publicationDate":"2023-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"tert-Butoxide-Mediated Protodeformylative Decarbonylation of α-Quaternary Homobenzaldehydes\",\"authors\":\"Ben Stokes, Xiaofeng Cai, Ritter V. Amsbaugh, Lauren J. Drake, Ravi M. A. Kotamraju, Nicholas Javier C. Licauco\",\"doi\":\"10.1055/a-2231-3108\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"\\n Tert-butoxide mediates the Haller–Bauer-type (protodeformylative) decarbonylation of readily accessed α-quaternary homobenzaldehydes and related compounds at room temperature, generating cumene products. Both geminal dialkyl and geminal diaryl substituents are tolerated. Gem-dimethyls are sufficient for decarbonylation of polycyclic arenyl substrates whereas monocyclic aromatic homobenzaldehydes require cyclic gem-dialkyls or gem-diaryls for significant decarbonylation.\",\"PeriodicalId\":22135,\"journal\":{\"name\":\"SynOpen\",\"volume\":\" 38\",\"pages\":\"\"},\"PeriodicalIF\":2.0000,\"publicationDate\":\"2023-12-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"SynOpen\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/a-2231-3108\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"SynOpen","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2231-3108","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
tert-Butoxide-Mediated Protodeformylative Decarbonylation of α-Quaternary Homobenzaldehydes
Tert-butoxide mediates the Haller–Bauer-type (protodeformylative) decarbonylation of readily accessed α-quaternary homobenzaldehydes and related compounds at room temperature, generating cumene products. Both geminal dialkyl and geminal diaryl substituents are tolerated. Gem-dimethyls are sufficient for decarbonylation of polycyclic arenyl substrates whereas monocyclic aromatic homobenzaldehydes require cyclic gem-dialkyls or gem-diaryls for significant decarbonylation.