- Making Dimethylamino a Transformable Directing Group by Nickel-Catalyzed C-N Borylation
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The dimethylamino (Me2N) group is arguably the most versatile functional group capable of highly efficient and site-selective directed aromatic functionalizations at the ortho-, meta-, and para-positions depending on reaction conditions. While the repertoire of Me2N-directed reactions is growing at a rapid pace, the lack of a general method to transform this group to other functionalities hampers its wider application in organic synthesis. Here we report nickel-catalyzed C-N borylations of aryl- and benzyl-dimethylamines that permit the conversion of a huge library of largely underutilized Me2N-containing organic molecules into various functional molecules by taking advantage of the wealth of existing C-B functionalization methods.
- Zhang, Hua,Hagihara, Shinya,Itami, Kenichiro
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supporting information
p. 16796 - 16800
(2015/11/16)
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- A study of BF3-promoted ortho lithiation of anilines and DFT calculations on the role of fluorine-lithium interactions
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(Figure Presented) Director's cut: The poor directing ability of the dimethylamino group in directed ortho metalation is altered by complexation to BF3, which makes it more strongly activating than methoxy and chloro groups. DFTcalculations of simplified lithiated intermediates reveal a small role of the inductive effect, but a distinctive F...Li interaction that leads to a F-Li distance which is remarkably similar to the C-Li distance.
- Kessar, Satinder V.,Singh, Paramjit,Singh, Kamal N.,Bharatam, Prasad V.,Sharma, Arvind K.,Lata, Sneh,Kaur, Amarjit
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supporting information; body text
p. 4703 - 4706
(2009/02/06)
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- Synthesis and molecular structures of (2-dialkylaminophenyl)alcohols and of 2-phenylaminoalkyl-dimethylaminobenzene derivatives
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N,N-Dimethyl-o-toluidine, N,N-dimethylaniline, and N,N-diethylaniline were treated with n-butyllithium-tmeda in diethyl ether-hexane solution to give o-lithioarylamines, which react with various electrophiles (benzophenone, dicyclohexyl ketone, benzaldehy
- Al-Masri, Harbi Tomah,Sieler, Joachim,L?nnecke, Peter,Blaurock, Steffen,Domasevitch, Konstantin,Hey-Hawkins, Evamarie
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p. 333 - 339
(2007/10/03)
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