The gomberg-bachmann reaction for the arylation of anilines with aryl diazotates
Simply aqueous sodium hydroxide is sufficient to exclude ionic side reactions and to prepare 2-aminobiphenyls from aryl diazotates and anilines through a new variant of the Gomberg-Bachmann reaction (see scheme). The metal-free reaction under basic conditions allows to exploit the highly radical-stabilizing effect of the aniline's free amino function for the first time, which leads to a so far unreached regioselectivity. Copyright
Pratsch, Gerald,Wallaschkowski, Tina,Heinrich, Markus R.
Radical Arylation of Anilines and Pyrroles via Aryldiazotates
The radical arylation of anilines and pyrroles can be achieved under transition-metal- and catalyst-free conditions by using aryldiazotates in strongly alkaline aqueous solutions. The aryldiazotates act as protected diazonium ions, which do not undergo azo coupling with electron-rich aromatic substrates, but can still serve as an aryl radical source at slightly elevated temperatures. Based on an improved preparation of aryldiazotates in aqueous solution, homolytic aromatic substitutions of anilines and pyrroles were conducted with good overall yields and high regioselectivity. Moreover, DFT calculations provided further mechanistic insights.
Hofmann, Josefa,Gans, Eva,Clark, Timothy,Heinrich, Markus R.
supporting information
p. 9647 - 9656
(2017/07/22)
The gomberg-bachmann reaction for the arylation of anilines with aryl diazotates
Simply aqueous sodium hydroxide is sufficient to exclude ionic side reactions and to prepare 2-aminobiphenyls from aryl diazotates and anilines through a new variant of the Gomberg-Bachmann reaction (see scheme). The metal-free reaction under basic conditions allows to exploit the highly radical-stabilizing effect of the aniline's free amino function for the first time, which leads to a so far unreached regioselectivity. Copyright
Pratsch, Gerald,Wallaschkowski, Tina,Heinrich, Markus R.
supporting information
p. 11555 - 11559,5
(2012/12/12)
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