Metallaphotoredox Perfluoroalkylation of Organobromides
Ruppert–Prakash type reagents (TMSCF3, TMSC2F5, and TMSC3F7) are readily available, air-stable, and easy-to-handle fluoroalkyl sources. Herein, we describe a mild, copper-catalyzed cross-coupling of these fluoroalkyl nucleophiles with aryl and alkyl bromides to produce a diverse array of trifluorome...
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| Veröffentlicht in: | Journal of the American Chemical Society 2020-11, Vol.142 (46), p.19480-19486 |
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| container_title | Journal of the American Chemical Society |
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| creator | Zhao, Xiangbo MacMillan, David W. C |
| description | Ruppert–Prakash type reagents (TMSCF3, TMSC2F5, and TMSC3F7) are readily available, air-stable, and easy-to-handle fluoroalkyl sources. Herein, we describe a mild, copper-catalyzed cross-coupling of these fluoroalkyl nucleophiles with aryl and alkyl bromides to produce a diverse array of trifluoromethyl, pentafluoroethyl, and heptafluoropropyl adducts. This light-mediated transformation proceeds via a silyl-radical-mediated halogen atom abstraction pathway, which enables perfluoroalkylation of a broad range of organobromides of variable steric and electronic demand. The utility of the method is demonstrated through the late-stage functionalization of several drug analogues. |
| doi_str_mv | 10.1021/jacs.0c09977 |
| format | Article |
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C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metallaphotoredox Perfluoroalkylation of Organobromides</atitle><jtitle>Journal of the American Chemical Society</jtitle><stitle>J AM CHEM SOC</stitle><addtitle>J. Am. Chem. Soc</addtitle><date>2020-11-18</date><risdate>2020</risdate><volume>142</volume><issue>46</issue><spage>19480</spage><epage>19486</epage><pages>19480-19486</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Ruppert–Prakash type reagents (TMSCF3, TMSC2F5, and TMSC3F7) are readily available, air-stable, and easy-to-handle fluoroalkyl sources. Herein, we describe a mild, copper-catalyzed cross-coupling of these fluoroalkyl nucleophiles with aryl and alkyl bromides to produce a diverse array of trifluoromethyl, pentafluoroethyl, and heptafluoropropyl adducts. 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| source | MEDLINE; ACS Publications; Web of Science - Science Citation Index Expanded - 2020<img src="https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg" /> |
| subjects | Alkylation Catalysis Chemistry Chemistry, Multidisciplinary Copper - chemistry Fluorocarbons - chemical synthesis Halogenation Hydrocarbons, Brominated - chemistry Oxidation-Reduction Photochemical Processes Physical Sciences Science & Technology Silanes - chemistry |
| title | Metallaphotoredox Perfluoroalkylation of Organobromides |
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