Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 13, Pages 2859-2866Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201400504
Keywords
iridium; isocyanides; isoquinolines; photochemistry; trifluoromethylation
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Funding
- 973 Program [2011CB935800, 2011CB808600]
- 863 program [2013AA092903]
- NSFC [21121091, 21472084, 21372115, 21290190]
- Natural Science Foundation of Jiangsu Province [BK2012012, BK20131266]
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A strategy has been developed for the regiospecific synthesis of 1-trifluoromethylisoquinoline derivatives. This strategy is enabled by a photoredox vinyl isocyanide insertion with the help of Umemoto's reagent. The methodology presented here provides an access to highly fuctionalized 1-trifluoromethylisoquinolines regiospecifically under mild conditions in good-to-excellent chemical yields. A detailed mechanism is proposed, which is supported by experiments and theoretical calculations.
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