{"title":"Palladium mediated domino heck redox cyclization of aromatic homoallylic alcohols to methylindanones","authors":"Vivek K. Mishra, Martin E. Maier, Manish Tiwari","doi":"10.1007/s13738-024-03053-3","DOIUrl":null,"url":null,"abstract":"<div><p>3-Methyl indanones are key synthetic building blocks for a variety of natural and useful synthetic compounds. Their synthesis is exceedingly difficult. Herein, we described a palladium (II) mediated intramolecular one-pot redox-relay cyclization of aromatic homoallylic alcohols to cyclic keto compounds. This catalytic system enabled direct conversion of homoallylic alcohols to corresponding indanones (3-methyl-1-indanones). Homoallylic alcohols were synthesized by reacting allyl magnesium bromide with corresponding aromatic aldehydes. The optimized reaction yielded up to 88% 3-methylindanones. Our findings enabled us to device a plausible mechanism for this one pot reaction.</p><h3>Graphical Abstract</h3>\n<div><figure><div><div><picture><img></picture></div></div></figure></div></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":null,"pages":null},"PeriodicalIF":2.2000,"publicationDate":"2024-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the Iranian Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s13738-024-03053-3","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
3-Methyl indanones are key synthetic building blocks for a variety of natural and useful synthetic compounds. Their synthesis is exceedingly difficult. Herein, we described a palladium (II) mediated intramolecular one-pot redox-relay cyclization of aromatic homoallylic alcohols to cyclic keto compounds. This catalytic system enabled direct conversion of homoallylic alcohols to corresponding indanones (3-methyl-1-indanones). Homoallylic alcohols were synthesized by reacting allyl magnesium bromide with corresponding aromatic aldehydes. The optimized reaction yielded up to 88% 3-methylindanones. Our findings enabled us to device a plausible mechanism for this one pot reaction.
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