88132-08-5Relevant academic research and scientific papers
Beyond directed ortho metalation: Ruthenium-catalyzed amide-directed C Ar-N activation/C-C coupling reaction of anthranilamides with organoboronates
Zhao, Yigang,Snieckus, Victor
supporting information, p. 3200 - 3203 (2014/07/08)
A new, catalytic, and general methodology for the synthesis of biaryls and heterobiaryls by the cross coupling of anthranilamide derivatives (o-NMe 2 benzamides) with aryl boroneopentylates is described. The reaction proceeds under catalytic RuH2(CO)(PPh3)3 conditions driven by the activation of the unreactive C-N bond by amide directing group (DG)-Ru catalyst chelation. High regioselectivity, orthogonality with the Suzuki-Miyaura reaction, operational simplicity, and convenient scale-up are features of these reactions which may lend themselves to industrial applications.
Contra-Friedel-Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation
Clayden, Jonathan,Stimson, Christopher C.,Keenan, Martine
, p. 1393 - 1394 (2008/02/03)
Directed metallation and sulfinylation yields sulfoxides which undergo ipso nucleophilic aromatic substitution with tertiary and secondary alkyllithiums, giving aromatic rings bearing alkyl groups generally incompatible with directed metallation methods and with regioselectivity complementary with classical Friedel-Crafts substitution. The Royal Society of Chemistry 2006.
Addition of ureas to arynes: Straightforward synthesis of benzodiazepine and benzodiazepine derivatives
Yoshida, Hiroto,Shirakawa, Eiji,Honda, Yuki,Hiyama, Tamejiro
, p. 3247 - 3249 (2007/10/03)
Seven- and eight-membered heterocycles are formed straightforwardly, in modest to high yields in this novel addition reaction of ureas to arynes (see scheme; R = alkoxy, alkyl, aryl). The reaction of a meta-substituted aryne affords the product with perfect regioselectivity, whereas a para-substituted aryne gives a mixture of regioisomers.
New approach to biomimetic transamination using bifunctional [1,3]-proton transfer catalysis in thioxanthenyl dioxide imines
Hjelmencrantz, Anders,Berg, Ulf
, p. 3585 - 3594 (2007/10/03)
A pyridoxamine equivalent, 9-aminothioxanthene 10,10-dioxide, has been designed that is capable of affording transamination in good to excellent yields of natural as well as artificial amino acids. Amidines and guanidines in catalytic amounts were capable of performing [1,3]-proton transfer in the imines under mild conditions, whereas various simple amines failed. The use of chiral catalysts resulted in modest asymmetric induction (ee ≤ 45%). The electronic dependence in para-substituted phenyl glyoxylate imines, isotope effects, and computational studies support a stepwise, bifunctional mechanism for amidine and guanidine catalysts. Attempts toward an autocatalytic model system are described.
