Copper‐Catalyzed Cross‐Dehydrogenative Coupling of N‐Iminoquinolinium Ylides with Secondary Amines

The copper-catalyzed cross-dehydrogenative coupling of N-iminoquinolinium ylides with secondary amines led to ortho-amino-substituted quinoline derivatives with high levels of regioselectivity in good yields. This direct C–H bond amination transformation employs CuI as the catalyst without the use of a ligand, external oxidant, or base. The reaction is operationally simple and can be conducted under mild conditions. The N-benzoyl directing group can be removed without any additional steps.

[1]  H. Ge,et al.  Recent Advances in First‐Row‐Transition‐Metal‐Catalyzed Dehydrogenative Cou­pling of C(sp3)–H Bonds , 2015 .

[2]  J. Yu,et al.  Benzoyl Peroxide Promoted Radical ortho‐Alkylation of Nitrogen Heteroaromatics with Simple Alkanes and Alcohols , 2015 .

[3]  A. Terent’ev,et al.  Cross-dehydrogenative coupling for the intermolecular C–O bond formation , 2015, Beilstein journal of organic chemistry.

[4]  Limin Wang,et al.  Silver-Catalyzed Direct C–H Arylation of N-Iminopyridinium Ylides with Arylboronic Acids , 2014, Synlett.

[5]  D. Wei,et al.  Copper-catalyzed direct amination of quinoline N-oxides via C-H bond activation under mild conditions. , 2014, Organic letters.

[6]  F. Patureau,et al.  Oxidative C-H amination reactions. , 2014, Chemical Society reviews.

[7]  Thomas Knauber,et al.  Dehydrierende Kreuzkupplungen von C sp 3‐H‐Bindungen: vielseitige Verfahren zur Bildung von C‐C‐Bindungen , 2014 .

[8]  Chao‐Jun Li,et al.  The cross-dehydrogenative coupling of C(sp3)-H bonds: a versatile strategy for C-C bond formations. , 2014, Angewandte Chemie.

[9]  Jun Wang,et al.  Palladium-catalyzed cross-dehydrogenative functionalization of C(sp(2))-H Bonds. , 2014, Chemistry, an Asian journal.

[10]  F. Shi,et al.  From N-benzoylpyridinium imides to pyrazolo[1,5-a]pyridines: a mechanistic discussion on a stoichiometric Cu protocol. , 2013, Organic & biomolecular chemistry.

[11]  P. Roepe,et al.  Quinoline drug-heme interactions and implications for antimalarial cytostatic versus cytocidal activities. , 2013, Journal of medicinal chemistry.

[12]  N. Jiao,et al.  Copper-catalyzed direct oxidative annulation of N-iminopyridinium ylides with terminal alkynes using O2 as oxidant. , 2013, Chemical communications.

[13]  J. Wang,et al.  Copper-catalyzed direct ortho-alkylation of N-iminopyridinium ylides with N-tosylhydrazones. , 2013, The Journal of organic chemistry.

[14]  Shannon S. Stahl,et al.  Kupferkatalysierte aerobe oxidative C‐H‐Funktionalisierungen: Trends und Erkenntnisse zum Mechanismus , 2011 .

[15]  Alison E Wendlandt,et al.  Copper-catalyzed aerobic oxidative C-H functionalizations: trends and mechanistic insights. , 2011, Angewandte Chemie.

[16]  J. Mousseau,et al.  Synthesis of 2- and 2,3-substituted pyrazolo[1,5-a]pyridines: scope and mechanistic considerations of a domino direct alkynylation and cyclization of N-iminopyridinium ylides using alkenyl bromides, alkenyl iodides, and alkynes. , 2011, The Journal of organic chemistry.

[17]  Yuan Cheng,et al.  From fragment screening to in vivo efficacy: optimization of a series of 2-aminoquinolines as potent inhibitors of beta-site amyloid precursor protein cleaving enzyme 1 (BACE1). , 2011, Journal of medicinal chemistry.

[18]  T. Nevalainen,et al.  Microwave-assisted synthesis of quinoline, isoquinoline, quinoxaline and quinazoline derivatives as CB2 receptor agonists. , 2011, Bioorganic & medicinal chemistry.

[19]  Kirandeep Kaur,et al.  Quinolines and structurally related heterocycles as antimalarials. , 2010, European journal of medicinal chemistry.

[20]  Caroline J. Scheuermann Beyond traditional cross couplings: the scope of the cross dehydrogenative coupling reaction. , 2010, Chemistry, an Asian journal.

[21]  J. Mousseau,et al.  Copper-catalyzed direct alkenylation of N-iminopyridinium ylides. , 2010, Angewandte Chemie.

[22]  J. Mousseau,et al.  Synthesis of 2-substituted pyrazolo[1,5-a]pyridines through cascade direct alkenylation/cyclization reactions. , 2010, Organic letters.

[23]  Chao‐Jun Li,et al.  Cross-dehydrogenative coupling reactions of sp3-hybridized C-H bonds. , 2010, Topics in current chemistry.

[24]  Chao‐Jun Li Cross-dehydrogenative coupling (CDC): exploring C-C bond formations beyond functional group transformations. , 2009, Accounts of chemical research.

[25]  J. Mousseau,et al.  Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine. , 2008, Journal of the American Chemical Society.

[26]  V. Gevorgyan,et al.  Direct transition metal-catalyzed functionalization of heteroaromatic compounds. , 2007, Chemical Society reviews.

[27]  Jonathan A. Ellman,et al.  The Direct Approach , 2007, Science.

[28]  T. Satoh,et al.  Catalytic Direct Arylation of Heteroaromatic Compounds , 2007 .

[29]  Mark E. Scott,et al.  Aryl-aryl bond formation by transition-metal-catalyzed direct arylation. , 2007, Chemical reviews.

[30]  Louis-Charles Campeau,et al.  Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules. , 2006, Chemical communications.

[31]  Claude Y. Legault,et al.  Highly efficient synthesis of O-(2,4-dinitrophenyl)hydroxylamine. Application to the synthesis of substituted N-benzoyliminopyridinium ylides. , 2003, The Journal of organic chemistry.

[32]  S. Campbell,et al.  2,4-Diamino-6,7-dimethoxyquinoline derivatives as alpha 1-adrenoceptor antagonists and antihypertensive agents. , 1988, Journal of medicinal chemistry.

[33]  A. Alhaider,et al.  Design, synthesis, and pharmacological activities of 2-substituted 4-phenylquinolines as potential antidepressant drugs. , 1985, Journal of medicinal chemistry.