63488-82-4Relevant academic research and scientific papers
A facile access for the C-N bond formation by transition metal-free oxidative coupling of benzylic C-H bonds and amides
Liu, Jie,Zhang, Heng,Yi, Hong,Liu, Chao,Lei, Aiwen
, p. 1323 - 1328 (2015/08/11)
Using 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) as the oxidant, we communicate an efficient oxidative C-N coupling of benzylic C-H bonds with amides to afford a series of amination products in good yields. A wide range of functional groups as well as various sulfonamides and carboxamides are well tolerated. Moreover, this reaction involves both the challenging C-H functionalization and C-N bond formation.
Expedient synthesis of functionalized triarylmethanols through tandem formation of geminal C-C and C-O bonds
Tian,Sui, Yi,Gu, Yonghong,Tian, Shi-Kai
, p. 3475 - 3479 (2013/02/22)
The rearrangement/oxidation of N,N-disubstituted anilines and the formal dehydrogenative cross-coupling of diarylmethanols with aniline derivatives have been developed for the preparation of symmetric and unsymmetric functionalized triarylmethanols. Both reactions proceed smoothly in trifluoroacetic acid in the presence of an inexpensive oxidant (manganese dioxide or potassium persulfate) and a catalytic amount of palladium diacetate to give a range of functionalized triarylmethanols in moderate to good yields and with extremely high regioselectivity. The two unprecedented reactions involve tandem formation of geminal C-C and C-O bonds, and they are synthetically useful, atom-efficient, and operationally simple.
A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates
Le Gall, Erwan,Pignon, Antoine,Martens, Thierry
, p. 997 - 1002 (2011/09/19)
A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates is described. This route involves the formation of an imine, which is used without isolation, followed by its activation
Superacid promoted reactions of N-acyliminium salts and evidence for the involvement of superelectrophiles
Zhang, Yiliang,DeSchepper, Daniel J.,Gilbert, Thomas M.,Sai, Kiran Kumar S.,Klumpp, Douglas A.
, p. 4032 - 4034 (2008/03/18)
Experimental and theoretical studies suggest the involvement of dicationic, superelectrophilic N-acyliminium ions in conversions catalyzed by superacids. The Royal Society of Chemistry.
Superacid-promoted reactions of N-acyliminium ions: An effective route to substituted 3-oxo-1,2,3,4-tetrahydroisoquinolines and related products
Zhang, Yiliang,Kindelin, Patrick J.,DeSchepper, Daniel J.,Zheng, Chong,Klumpp, Douglas A.
, p. 1775 - 1780 (2008/01/27)
Intramolecular cyclizations involving N-acyliminium ions are shown to give products in good yields from reactions with CF3SO3H (triflic acid). The resulting 3-oxo-1,2,3,4-tetrahydroisoquinolines have been converted in high yields to 1,2-diaryl-1,2,3,4-tetrahydroisoquinolines, which have been recently shown to be selective estrogen receptor modulators. In a reaction using a chiral N-acyliminium ion, cyclization is found to occur in moderately high diastereoselectivity. Several examples of intermolecular triflic acid-promoted reactions are also reported. Georg Thieme Verlag Stuttgart.
