Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction

A benzaldehyde-mediated photoredox reaction for the α-heteroarylation of amides (α to nitrogen) and ethers through cross-dehydrogenative coupling (CDC).

[1]  J. Wirz,et al.  Photohydration of Benzophenone in Aqueous Acid , 2003 .

[2]  D. MacMillan,et al.  A general strategy for organocatalytic activation of C-H bonds via photoredox catalysis: direct arylation of benzylic ethers. , 2014, Journal of the American Chemical Society.

[3]  Y. Tu,et al.  Direct Sp3α-C-H activation and functionalization of alcohol and ether. , 2011, Chemical Society reviews.

[4]  Lina Zhang,et al.  Light promoted aqueous phase amine synthesis via three-component coupling reactions , 2013 .

[5]  F. Fontana,et al.  Recent developments of free-radical substitutions of heteroaromatic bases , 1989 .

[6]  Lei Wang,et al.  Direct amidation of azoles with formamides via metal-free C-H activation in the presence of tert-butyl perbenzoate. , 2011, Chemical communications.

[7]  Xiaobo Huang,et al.  Unexpected TFA-catalyzed tandem reaction of benzo[d]oxazoles with 2-oxo-2-arylacetic acids: synthesis of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones and cephalandole A , 2014 .

[8]  L. Palmisano,et al.  Sunlight induced functionalisation of some heterocyclic bases in the presence of polycrystalline TiO2. , 2003, Chemical communications.

[9]  F. Fontana,et al.  A novel, selective free-radical carbamoylation of heteroaromatic bases by Ce(IV) oxidation of formamide, catalysed by N-hydroxyphthalimide , 2002 .

[10]  K. P. Cole,et al.  Photoredox Catalysis in a Complex Pharmaceutical Setting: Toward the Preparation of JAK2 Inhibitor LY2784544 , 2014, The Journal of organic chemistry.

[11]  H. Niu,et al.  Radical route for the alkylation of purine nucleosides at C6 via Minisci reaction. , 2014, Organic letters.

[12]  L. Vares,et al.  An alternative synthesis of the NMDA antagonist CGS 19755 via free radical carbamoylation of ethyl isonicotinate. , 1995, Acta chemica Scandinavica.

[13]  Photo-organocatalysis of atom-transfer radical additions to alkenes. , 2014, Angewandte Chemie.

[14]  Frank Glorius,et al.  Dual catalysis sees the light: combining photoredox with organo-, acid, and transition-metal catalysis. , 2014, Chemistry.

[15]  Yi Pan,et al.  Cu-catalyzed cross-dehydrogenative coupling reactions of (benzo)thiazoles with cyclic ethers. , 2013, Organic letters.

[16]  D. MacMillan,et al.  Direct α-arylation of ethers through the combination of photoredox-mediated C-H functionalization and the Minisci reaction. , 2015, Angewandte Chemie.

[17]  Cameron J. Cowden,et al.  Use of N-protected amino acids in the Minisci radical alkylation. , 2003, Organic letters.

[18]  T. Opatz,et al.  Radical Addition to Iminium Ions and Cationic Heterocycles , 2014, Molecules.

[19]  J. Zeng,et al.  Regiospecific Minisci acylation of phenanthridine via thermolysis or photolysis , 2014 .

[20]  Christopher K Prier,et al.  Discovery of an α-Amino C–H Arylation Reaction Using the Strategy of Accelerated Serendipity , 2011, Science.

[21]  Rangappa S. Keri,et al.  A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry. , 2015, European journal of medicinal chemistry.

[22]  Laura Furst,et al.  Light‐Assisted Cross‐Dehydrogenative‐Coupling Reactions , 2015 .

[23]  A. Katritzky,et al.  Preparation of cyanopyridines by direct cyanation , 2005 .

[24]  O. Daugulis,et al.  Copper-catalyzed cyanation of heterocycle carbon-hydrogen bonds. , 2010, Organic letters.

[25]  D. MacMillan,et al.  Amine α-heteroarylation via photoredox catalysis: a homolytic aromatic substitution pathway. , 2014, Chemical science.

[26]  J. Hartwig,et al.  Cyanation of arenes via iridium-catalyzed borylation. , 2010, Journal of the American Chemical Society.

[27]  Lei Shi,et al.  Photoredox functionalization of C-H bonds adjacent to a nitrogen atom. , 2012, Chemical Society reviews.

[28]  F. Fleming,et al.  Nitrile-containing pharmaceuticals: efficacious roles of the nitrile pharmacophore. , 2010, Journal of medicinal chemistry.

[29]  Hua Wang,et al.  Oxone-mediated oxidative carbon-heteroatom bond cleavage: synthesis of benzoxazinones from benzoxazoles with α-oxocarboxylic acids , 2014 .

[30]  Danielle M. Schultz,et al.  Solar Synthesis: Prospects in Visible Light Photocatalysis , 2014, Science.

[31]  Anlong Xu,et al.  β-Carboline Alkaloids: Biochemical and Pharmacological Functions , 2007 .

[32]  Novel and direct oxidative cyanation reactions of heteroaromatic compounds mediated by a hypervalent iodine(III) reagent. , 2005, Organic letters.

[33]  Chuo Chen,et al.  Visible light-promoted metal-free C-H activation: diarylketone-catalyzed selective benzylic mono- and difluorination. , 2013, Journal of the American Chemical Society.

[34]  N. Yang,et al.  Paterno-Buechi reactions of aromatic aldehydes with 2-butenes and their implication on the rate of intersystem crossing of aromatic aldehydes , 1973 .

[35]  D. Dondi,et al.  Tetrabutylammonium Decatungstate (Chemo)selective Photocatalyzed, Radical C ? H Functionalization in Amides , 2008 .

[36]  T. Lu,et al.  Synthesis and structure of the β-carboline derivatives and their binding intensity with cyclin-dependent kinase 2. , 2012, Chemical & pharmaceutical bulletin.

[37]  D. MacMillan,et al.  Activation of C–H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases , 2014, Journal of the American Chemical Society.

[38]  Wen-Jing Xiao,et al.  Visible-light photoredox catalysis. , 2012, Angewandte Chemie.

[39]  Corey R J Stephenson,et al.  Visible light photoredox catalysis: applications in organic synthesis. , 2011, Chemical Society reviews.

[40]  D. Hunkeler Mechanism and kinetics of the persulfate-initiated polymerization of acrylamide , 1991 .

[41]  S. R. Slaughter,et al.  FDA approval of doxylamine-pyridoxine therapy for use in pregnancy. , 2014, The New England journal of medicine.

[42]  S. Nordeen,et al.  Photocatalytic synthesis of dihydrobenzofurans by oxidative [3+2] cycloaddition of phenols. , 2014, Angewandte Chemie.

[43]  D. MacMillan,et al.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. , 2013, Chemical reviews.

[44]  M. Duncton Minisci reactions: Versatile CH-functionalizations for medicinal chemists , 2011 .

[45]  Jagan M. R. Narayanam,et al.  Friedel-Crafts amidoalkylation via thermolysis and oxidative photocatalysis. , 2012, The Journal of organic chemistry.