{"title":"Preparation of N-Formylamides by Oxidative Cleavage of N-Acylaminoacids","authors":"Nick Kilenyi","doi":"10.15227/orgsyn.099.0029","DOIUrl":"https://doi.org/10.15227/orgsyn.099.0029","url":null,"abstract":"","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67341353","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Discussion Addendum for: Asymmetric Michael Reaction of Aldehydes and Nitroalkenes","authors":"Y. Hayashi","doi":"10.15227/orgsyn.099.0068","DOIUrl":"https://doi.org/10.15227/orgsyn.099.0068","url":null,"abstract":"","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67341830","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"A Convenient Method for the Removal of Tetrabutylammonium Salts from Desilylation Reactions","authors":"L. McDermott","doi":"10.15227/orgsyn.099.0053","DOIUrl":"https://doi.org/10.15227/orgsyn.099.0053","url":null,"abstract":"4-Bromophenol (2). A single-necked (24/40 joint) 250 mL round-bottomed flask is equipped with a Teflon-coated magnetic stir bar (3.0 x 1.5 cm, footballshaped). The apparatus is flame-dried under reduced pressure and cooled to 23 °C under an atmosphere of nitrogen. The flask is then equipped with a rubber septum and then placed under positive pressure of nitrogen using a nitrogen inlet. To the flask is then added (4-bromophenol)(tertbutyl)dimethylsilane (1) (4.5 g, 3.8 mL, 16 mmol, 1.0 equiv) (Note 2) via syringe. Then, dry THF (30 mL) (Note 3) is added at 23 °C to the flask via syringe and stirring is started (300 rpm). After one min of stirring, tetrabutylammonium fluoride solution (19 mL, 1.0 M in THF, 19 mmol, 1.2 equiv) (Note 4) is added via syringe dropwise over five min (Figure 1A). The reaction mixture is then allowed to stir (300 rpm) at 23 °C for 30 min (Note 5). Then, the rubber septum is removed, and calcium carbonate (8.2 g, 82 mmol, 5.3 equiv) (Note 6) is added in one portion followed by Dowex 50WX8, 200–400 mesh, ion exchange resin (24 g) (Note 7) in two equal portions using a funnel to assist with the addition. To the reaction mixture is then added methanol (60 mL) (Figure 1B) (Note 8), the rubber septum is Br OTBS i. TBAF, THF, 23 °C","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67341750","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Organocatalytic Dimerization of Succinaldehyde","authors":"Steven H. Bennett","doi":"10.15227/orgsyn.099.0139","DOIUrl":"https://doi.org/10.15227/orgsyn.099.0139","url":null,"abstract":"","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67341706","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Peng-Jui Chen, Aidan M Kelly, Daniel J Blair, Martin D Burke
{"title":"Preparation of MIDA Anhydride and Reaction with Boronic Acids.","authors":"Peng-Jui Chen, Aidan M Kelly, Daniel J Blair, Martin D Burke","doi":"10.15227/orgsyn.099.0092","DOIUrl":"https://doi.org/10.15227/orgsyn.099.0092","url":null,"abstract":"A. MIDA Anhydride (1). A 500 mL single-necked, 24/40 round-bottomed flask equipped with a 5 x 2 cm Teflon-coated magnetic stirring bar is charged with methyliminodiacetic acid (40.0 g, 270 mmol, 1.00 equiv)(Notes 2 and 3), capped with a rubber septum and evacuated and backfilled with nitrogen via 20 G needle. Acetic anhydride (140 mL, 1.49 mol, 5.52 equiv) (Note 4) is added via syringe as a single portion to form a colorless suspension. This is immediately followed by the addition of pyridine (3.30 mL, 40.5 mmol, 0.15 eq.)(Note 5) in a single portion (Figure 1B). The flask is stirred under HO O N Me OH O","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10428519/pdf/nihms-1920052.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10095845","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of Triphenylene via the Palladium–Catalyzed Annulation of Benzyne","authors":"Katie A. Spence","doi":"10.15227/orgsyn.099.0174","DOIUrl":"https://doi.org/10.15227/orgsyn.099.0174","url":null,"abstract":"","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67341474","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Transformation of a N,N-Dimethylaniline N-oxide into a Tetrahydroquinoline Scaffold via a Formal Polonovski-Povarov Reaction","authors":"Elizabeth L. Isaac","doi":"10.15227/orgsyn.099.0381","DOIUrl":"https://doi.org/10.15227/orgsyn.099.0381","url":null,"abstract":"","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67342006","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}