to nucleophiles 3  a  n ( 0.2  mmol ) in 1,4dioxane ( or nmp ) solution ( 1.5  ml ) , diazotriflone 2 ( 0.4  mmol ) and cucl ( or cuf2 ) ( 0.04  mmol ) were added under n2 atmosphere in the presence or absence of additives described in schemes  3 and 4 . the mixture was then heated at 50  c for 12 or 24  h. the mixture was diluted with et2o ( 30  ml ) , washed once with h2o ( 20  ml ) and brine ( 20  ml ) , and the organic phase was dried by dry na2so4 . solvent was removed in vacuo , and the sample purified by column chromatography to afford scf3products 4  a  n . to aryl iodides 3  o  t ( 0.2  mmol ) in dmf solution ( 2.5  ml ) in a sealed tube , diazotriflone 2 ( 0.5  mmol ) and cu ( 1.0  mmol ) were added under n2 atmosphere , the tube was sealed , and the mixture was heated at 50  c for 12  h. the temperature was increased to 120  c and heated for another 12  h. the mixture was diluted by et2o ( 30  ml ) and washed once with h2o ( 20  ml ) and brine ( 20  ml ) , and the organic phase was dried by dry na2so4 . solvent was removed in vacuo , and the sample purified by column chromatography ( or preparative thinlayer plates ) to afford scf3products 4 
 o  t . complete synthetic protocols together with characterization data , including spectra for all compounds described herein , are provided in the supporting information . to nucleophiles 3  a  n ( 0.2  mmol ) in 1,4dioxane ( or nmp ) solution ( 1.5  ml ) , diazotriflone 2 ( 0.4  mmol ) and cucl ( or cuf2 ) ( 0.04  mmol ) were added under n2 atmosphere in the presence or absence of additives described in schemes  3 and 4 . the mixture was then heated at 50  c for 12 or 24  h. the mixture was diluted with et2o ( 30  ml ) , washed once with h2o ( 20  ml ) and brine ( 20  ml ) , and the organic phase was dried by dry na2so4 . solvent was removed in vacuo , and the sample purified by column chromatography to afford scf3products 4  a  n . to aryl iodides 3  o  t ( 0.2  mmol ) in dmf solution ( 2.5  ml ) in a sealed tube , diazotriflone 2 ( 0.5  mmol ) and cu ( 1.0  mmol ) were added under n2 atmosphere , the tube was sealed , and the mixture was heated at 50  c for 12  h. the temperature was increased to 120  c and heated for another 12  h. the mixture was diluted by et2o ( 30  ml ) and washed once with h2o ( 20  ml ) and brine ( 20  ml ) , and the organic phase was dried by dry na2so4 . solvent was removed in vacuo , and the sample purified by column chromatography ( or preparative thinlayer plates ) to afford scf3products 4 
 o  t . complete synthetic protocols together with characterization data , including spectra for all compounds described herein , are provided in the supporting information . as a service to our authors and readers , this journal provides supporting information supplied by the authors . such materials are peer reviewed and may be reorganized for online delivery , but are not copyedited or typeset . technical support issues arising from supporting information ( other than missing files ) should be addressed to the authors .
abstract2diazo1phenyl2((trifluoromethyl)sulfonyl)ethan1one ( diazotriflone ) ( 2 ) is not only a building block but also a reagent . in this study , 
 diazotriflone , which was originally used for the synthesis of lactam triflones as a trifluoromethanesulfonyl ( so2cf3 ) building block under catalystfree thermal conditions , is redisclosed as an effective electrophilic trifluoromethylthiolation reagent under copper catalysis . 
 a broad set of enamines , indoles , keto esters , pyrroles , and anilines were nicely transformed into corresponding trifluoromethylthio ( scf3 ) compounds in good to high yields by diazotriflone under copper catalysis via an electrophilictype reaction . a couplingtype trifluoromethylthiolation reaction of aryl iodides 
 was also realized by diazotriflone in acceptable yields .