Nucleophilic Trifluoromethylation of Carbonyl Compounds: Trifluoroacetaldehyde Hydrate as a Trifluoromethyl Source
A feasible nucleophilic trifluoromethylating protocol has been developed using trifluoroacetaldehyde hydrate as an atom-economical trifluoromethyl source. The reaction was found to be applicable to the nucleophilic trifluoromethylation of a broad spectrum of carbonyl compounds with satisfactory yiel...
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| Veröffentlicht in: | Journal of organic chemistry 2013-04, Vol.78 (7), p.3300-3305 |
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| container_end_page | 3305 |
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| container_issue | 7 |
| container_start_page | 3300 |
| container_title | Journal of organic chemistry |
| container_volume | 78 |
| creator | Prakash, G. K. Surya Zhang, Zhe Wang, Fang Munoz, Socrates Olah, George A |
| description | A feasible nucleophilic trifluoromethylating protocol has been developed using trifluoroacetaldehyde hydrate as an atom-economical trifluoromethyl source. The reaction was found to be applicable to the nucleophilic trifluoromethylation of a broad spectrum of carbonyl compounds with satisfactory yields in general. DFT calculations have been performed to provide mechanistic insight into the present and related reactions employing 2,2,2-trifluoro-1-methoxyethanol and hexafluoroacetone hydrate. |
| doi_str_mv | 10.1021/jo400202w |
| format | Article |
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DFT calculations have been performed to provide mechanistic insight into the present and related reactions employing 2,2,2-trifluoro-1-methoxyethanol and hexafluoroacetone hydrate.</description><identifier>ISSN: 0022-3263</identifier><identifier>ISSN: 1520-6904</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo400202w</identifier><identifier>PMID: 23425346</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Acetaldehyde - analogs & derivatives ; Acetaldehyde - chemistry ; Acetone - analogs & derivatives ; Acetone - chemical synthesis ; Acetone - chemistry ; carbonyl compounds ; chemical reactions ; chemical structure ; Ethylene Glycols - chemical synthesis ; Ethylene Glycols - chemistry ; Fluorocarbons - chemical synthesis ; Fluorocarbons - chemistry ; Lewis bases ; Methylation ; Molecular Structure ; organic chemistry</subject><ispartof>Journal of organic chemistry, 2013-04, Vol.78 (7), p.3300-3305</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a508t-461f54884081fe608f9e5c9a0e310cde462cc0f6faeefadf69dffa87b72c99d3</citedby><cites>FETCH-LOGICAL-a508t-461f54884081fe608f9e5c9a0e310cde462cc0f6faeefadf69dffa87b72c99d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo400202w$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo400202w$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23425346$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Prakash, G. 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DFT calculations have been performed to provide mechanistic insight into the present and related reactions employing 2,2,2-trifluoro-1-methoxyethanol and hexafluoroacetone hydrate.</description><subject>Acetaldehyde - analogs & derivatives</subject><subject>Acetaldehyde - chemistry</subject><subject>Acetone - analogs & derivatives</subject><subject>Acetone - chemical synthesis</subject><subject>Acetone - chemistry</subject><subject>carbonyl compounds</subject><subject>chemical reactions</subject><subject>chemical structure</subject><subject>Ethylene Glycols - chemical synthesis</subject><subject>Ethylene Glycols - chemistry</subject><subject>Fluorocarbons - chemical synthesis</subject><subject>Fluorocarbons - chemistry</subject><subject>Lewis bases</subject><subject>Methylation</subject><subject>Molecular Structure</subject><subject>organic chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU1v1DAQhi0EotvCgT-AckGCQ6i_k3BAQitKkapyYO_WrD1mUznxYieg_HtcbVlKhYQvI9nPPBrPS8gLRt8yytn5TZSUcsp_PiIrpjitdUflY7Iql7wWXIsTcprzDS1HKfWUnHAhuRJSr0i6nm3AuN_1obfVJvU-zDHFAafdEmDq41hFX60hbeO4hGodh32cR5ff_WHB4gTB4W5xWF0uLsGEFeQKHuqqr3FOFp-RJx5Cxud39YxsLj5u1pf11ZdPn9cfrmpQtJ1qqZlXsm0lbZlHTVvfobIdUBSMWodSc2up1x4QPTivO-c9tM224bbrnDgj7w_a_bwd0FkcpwTB7FM_QFpMhN78_TL2O_Mt_jBCN6rtdBG8vhOk-H3GPJmhzxZDgBHjnA2_XWfbyEb9F2WCS9Gxwhb0zQG1Keac0B8nYtTcpmmOaRb25f0vHMnf8RXg1QEAm0vfnMay0H-IfgGia6r6</recordid><startdate>20130405</startdate><enddate>20130405</enddate><creator>Prakash, G. 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| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2013-04, Vol.78 (7), p.3300-3305 |
| issn | 0022-3263 1520-6904 1520-6904 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Acetaldehyde - analogs & derivatives Acetaldehyde - chemistry Acetone - analogs & derivatives Acetone - chemical synthesis Acetone - chemistry carbonyl compounds chemical reactions chemical structure Ethylene Glycols - chemical synthesis Ethylene Glycols - chemistry Fluorocarbons - chemical synthesis Fluorocarbons - chemistry Lewis bases Methylation Molecular Structure organic chemistry |
| title | Nucleophilic Trifluoromethylation of Carbonyl Compounds: Trifluoroacetaldehyde Hydrate as a Trifluoromethyl Source |
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