322645-73-8Relevant academic research and scientific papers
Nucleophilic bromodifluoromethylation of iminium ions
Tsymbal, Artem V.,Kosobokov, Mikhail D.,Levin, Vitalij V.,Struchkova, Marina I.,Dilman, Alexander D.
, p. 7831 - 7835 (2015/03/18)
A method for bromodifluoromethylation of iminium ions using Me3SiCF2Br is described. The reaction involves room temperature activation of the silicon reagent by HMPA to generate difluorocarbene, which upon interacting with excess of bromide ion provides bromodifluoromethyl carbanionic species. The iminium electrophiles are generated in situ from aldehydes, secondary amines, proton sponge, and silyl triflate. The reaction can be extended for introduction of chlorodifluoromethyl and iododifluoromethyl groups.
Palladium catalysed aryl amination reactions in supercritical carbon dioxide
Smith, Catherine J.,Tsang, Melanie W.S.,Holmes, Andrew B.,Danheiser, Rick L.,Tester, Jefferson W.
, p. 3767 - 3781 (2007/10/03)
Palladium catalysed C-N bond formation in supercritical carbon dioxide has been accomplished. Carbamic acid formation is avoided in part through the use of an N-silylamine as the coupling partner. Employing a catalyst system of Pd 2dba3 (1 mol%) and 2-dicyclohexylphosphino-2′, 4′,6′-triisopropyl-1,1′-biphenyl (X-Phos) (2 mol%) enabled the catalytic amination of aryl bromides and chlorides with N-silylanilines to be realised in excellent yield. Extension of the methodology to the N-arylation of N-silyldiarylamines, N-silylazoles and N-silylsulfonamides is reported. The Royal Society of Chemistry 2005.
METHODS OF AMINATION
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Page/Page column 24-25, (2010/02/14)
A method of synthesising a compound of formula I: comprising the step of reacting a moiety of formula II: with a moiety of formula III: in compressed carbon dioxide in the presence of a transition metal catalyst and a base, wherein L is a labile leaving group; RN1 is optionally substituted C5-20 aryl; RN2is selected from optionally substituted C5-20aryl, optionally substituted C3-20 heterocyclyl, optionally substituted C3-7 alkyl, and optionally substituted sulfonyl; RN3 is selected from H and optionally substituted C1-7 alkyl, C3-20 heterocyclyl and C5-20aryl; or RN2 and RN3 together with the nitrogen atom to which they are attached form optionally substituted nitrogen-containing C3-20heterocylyl or C5-20 heteroaryl; and R1 R2 and R3 are independently selected from optionally substituted C1-7alkyl, C5-20 aryl, C3-20 heterocyclyl, hydroxy, halo, amino and C1-7 alkoxy, or two of R1, R2 and R3, together with the silicon atom to which they are attached, may form a silicon containing C5-7 heterocyclyl group.
