Metal-free amidation of ether sp3 C–H bonds with sulfonamides using PhI(OAc)2

Campos, Jesús; Goforth, Sarah K.; Crabtree, Robert H.; Gunnoe, T. Brent

doi:10.1039/C4RA09665G

Metal-free amidation of ether sp³ C–H bonds with sulfonamides using PhI(OAc)₂

Journal Article · Wed Sep 17 00:00:00 EDT 2014 · RSC Advances

DOI:https://doi.org/10.1039/C4RA09665G· OSTI ID:1607794

Campos, Jesús ^[1]; Goforth, Sarah K. ^[2]; Crabtree, Robert H. ^[3]; Gunnoe, T. Brent ^[2]

Yale Univ., New Haven, CT (United States); University of Virginia
Univ. of Virginia, Charlottesville, VA (United States)
Yale Univ., New Haven, CT (United States)

A selective protocol for the metal-free α-C–H amidation of ethers using sulfonamides and hypervalent iodine oxidants has been developed. The absence of precious metals and the conditions employed make the method environmentally attractive. A number of cyclic and acyclic, linear and branched ethers have been successfully amidated, and a broad sulfonamide scope has been demonstrated. Two unusual reactions, namely the amidation of an unactivated tert-butyl group and a tandem C–C coupling reaction, are further described here.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Virginia, Charlottesville, VA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: SC0001298

OSTI ID:: 1607794

Alternate ID(s):: OSTI ID: 1168236
OSTI ID: 1384269

Journal Information:: RSC Advances, Journal Name: RSC Advances Journal Issue: 89 Vol. 4; ISSN 2046-2069; ISSN RSCACL

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (80)

Catalytic C-H Amination with Nitrenes Dauban, Philippe; Dodd, Robert H. Amino Group Chemistry: From Synthesis to the Life Sciences https://doi.org/10.1002/9783527621262.ch2	book	November 2007
Rhodium-Catalyzed C-H Aminations Lebel, Helene Catalyzed Carbon‐Heteroatom Bond Formation https://doi.org/10.1002/9783527633388.ch5	book	October 2010
Rh-, Ag-, and Cu-Catalyzed C-N Bond Formation Dauban, Philippe; Lescot, Camille; Diaz-Requejo, M. Mar Innovative Catalysis in Organic Synthesis: Oxidation, Hydrogenation, and C-X Bond Forming Reactions https://doi.org/10.1002/9783527646586.ch12	book	January 2012
Intermolecular Hydrogen Abstraction Reaction between Nitrogen Radicals in Purine Rings and Alkyl Ethers: A Highly Selective Method for the Synthesis of N-9 Alkylated Purine Nucleoside Derivatives Guo, Hai-Ming; Xia, Chao; Niu, Hong-Ying Advanced Synthesis & Catalysis, Vol. 353, Issue 1 https://doi.org/10.1002/adsc.201000682	journal	January 2011
Rh-Catalyzed Amination of Ethereal CαH Bonds: A Versatile Strategy for the Synthesis of Complex Amines Williams Fiori, Kristin; Fleming, James J.; Du Bois, Justin Angewandte Chemie, Vol. 116, Issue 33 https://doi.org/10.1002/ange.200460791	journal	August 2004
A Copper(II)-Catalyzed Aza-Friedel-Crafts Reaction ofN-(2-Pyridyl)sulfonyl Aldimines: Synthesis of Unsymmetrical Diaryl Amines and Triaryl Methanes Esquivias, Jorge; Gómez Arrayás, Ramón; Carretero, Juan C. Angewandte Chemie, Vol. 118, Issue 4 https://doi.org/10.1002/ange.200503305	journal	January 2006
Rh-Catalyzed Amination of Ethereal CαH Bonds: A Versatile Strategy for the Synthesis of Complex Amines Williams Fiori, Kristin; Fleming, James J.; Du Bois, Justin Angewandte Chemie International Edition, Vol. 43, Issue 33 https://doi.org/10.1002/anie.200460791	journal	August 2004
Recent Advances in Catalytic Intramolecular CH Aminations Davies, Huw M. L.; Long, Matthew S. Angewandte Chemie International Edition, Vol. 44, Issue 23 https://doi.org/10.1002/anie.200500554	journal	June 2005
A Copper(II)-Catalyzed Aza-Friedel-Crafts Reaction ofN-(2-Pyridyl)sulfonyl Aldimines: Synthesis of Unsymmetrical Diaryl Amines and Triaryl Methanes Esquivias, Jorge; Gómez Arrayás, Ramón; Carretero, Juan C. Angewandte Chemie International Edition, Vol. 45, Issue 4 https://doi.org/10.1002/anie.200503305	journal	January 2006
Direct Azole Amination: CH Functionalization as a New Approach to Biologically Important Heterocycles Armstrong, Alan; Collins, James C. Angewandte Chemie International Edition, Vol. 49, Issue 13 https://doi.org/10.1002/anie.200906750	journal	February 2010
Organocatalytic, Oxidative, Intramolecular CH Bond Amination and Metal-free Cross-Amination of Unactivated Arenes at Ambient Temperature Antonchick, Andrey P.; Samanta, Rajarshi; Kulikov, Katharina Angewandte Chemie International Edition, Vol. 50, Issue 37 https://doi.org/10.1002/anie.201102984	journal	July 2011
Enantioselective Metal-Free Diamination of Styrenes Röben, Caren; Souto, José A.; González, Yolanda Angewandte Chemie International Edition, Vol. 50, Issue 40 https://doi.org/10.1002/anie.201103077	journal	August 2011
Microwave Effects in Organic Synthesis: Myth or Reality? Kappe, C. Oliver; Pieber, Bartholomäus; Dallinger, Doris Angewandte Chemie International Edition, Vol. 52, Issue 4 https://doi.org/10.1002/anie.201204103	journal	December 2012
Defined Hypervalent Iodine(III) Reagents Incorporating Transferable Nitrogen Groups: Nucleophilic Amination through Electrophilic Activation Souto, José A.; Martínez, Claudio; Velilla, Irene Angewandte Chemie International Edition, Vol. 52, Issue 4 https://doi.org/10.1002/anie.201206420	journal	December 2012
Iodine(III)-Promoted Intermolecular Diamination of Alkenes Souto, José A.; González, Yolanda; Iglesias, Alvaro Chemistry - An Asian Journal, Vol. 7, Issue 5 https://doi.org/10.1002/asia.201101025	journal	March 2012
N ‐Tosyloxycarbamates as Reagents in Rhodium‐Catalyzed CH Amination Reactions Huard, Kim; Lebel, Hélène Chemistry - A European Journal, Vol. 14, Issue 20 https://doi.org/10.1002/chem.200702027	journal	July 2008
A Metal-Free Route to 2-Aminooxazoles by Taking Advantage of the Unique Ring Opening of Benzoxazoles and Oxadiazoles with Secondary Amines Joseph, Jomy; Kim, Ji Young; Chang, Sukbok Chemistry - A European Journal, Vol. 17, Issue 30 https://doi.org/10.1002/chem.201100910	journal	June 2011
Oxidation of Benzylic Alcohols and Ethers to Carbonyl Derivatives by Nitric Acid in Dichloromethane. Strazzolini, Paolo; Runcio, Antonio ChemInform, Vol. 34, Issue 22 https://doi.org/10.1002/chin.200322048	journal	June 2003
A Novel Sulfonamidoglycosylation of Glycals. Colinas, Pedro A.; Bravo, Rodolfo D. ChemInform, Vol. 35, Issue 13 https://doi.org/10.1002/chin.200413155	journal	March 2004
Rh-Catalyzed Amination of Ethereal Cα—H Bonds: A Versatile Strategy for the Synthesis of Complex Amines. Fiori, Kristin Williams; Fleming, James J.; Du Bois, Justin ChemInform, Vol. 35, Issue 50 https://doi.org/10.1002/chin.200450135	journal	December 2004
Amination of Ethers Using Chloramine-T Hydrate and a Copper(I) Catalyst. Albone, David P.; Challenger, Stephen; Derrick, Andrew M. ChemInform, Vol. 36, Issue 20 https://doi.org/10.1002/chin.200520044	journal	May 2005
Microwaves in Organic Synthesis. Thermal and Non-Thermal Microwave Effects de la Hoz, Antonio; Diaz-Ortiz, Angel; Moreno, Andres ChemInform, Vol. 36, Issue 21 https://doi.org/10.1002/chin.200521275	journal	May 2005
Sulfonamidoglycosylation of Methyl Ribofuranosides: A Novel Approach to Furanosylsulfonamides. Colinas, Pedro A.; Bravo, Rodolfo D. ChemInform, Vol. 36, Issue 26 https://doi.org/10.1002/chin.200526131	journal	June 2005
Recent Advances in Catalytic Intramolecular C—H Aminations Davies, Huw M. L.; Long, Matthew S. ChemInform, Vol. 36, Issue 37 https://doi.org/10.1002/chin.200537255	journal	September 2005
N-Tosyloxycarbamates as a Source of Metal Nitrenes: Rhodium-Catalyzed C—H Insertion and Aziridination Reactions. Lebel, Helene; Huard, Kim; Lectard, Sylvain ChemInform, Vol. 37, Issue 7 https://doi.org/10.1002/chin.200607039	journal	February 2006
α-Amidation of Cyclic Ethers Catalyzed by Simple Copper Salt and a Mild and Efficient Preparation Method for α,ω-Amino Alcohols. He, Ling; Yu, Jing; Zhang, Ji ChemInform, Vol. 38, Issue 42 https://doi.org/10.1002/chin.200742058	journal	October 2007
Oxidation of Benzylic Alcohols and Ethers to Carbonyl Derivatives by Nitric Acid in Dichloromethane Strazzolini, Paolo; Runcio, Antonio European Journal of Organic Chemistry, Vol. 2003, Issue 3 https://doi.org/10.1002/ejoc.200390090	journal	February 2003
Metal-Free Oxidative Carbon-Heteroatom Bond Formation Through C-H Bond Functionalization: Metal-Free Oxidative Carbon-Heteroatom Bond Formation Samanta, Rajarshi; Matcha, Kiran; Antonchick, Andrey P. European Journal of Organic Chemistry, Vol. 2013, Issue 26 https://doi.org/10.1002/ejoc.201300286	journal	June 2013
In vitro antitumor activity of N-glycosyl sulfonamides Crespo, Rosana; de Bravo, Margarita G.; Colinas, Pedro A. Bioorganic & Medicinal Chemistry Letters, Vol. 20, Issue 22 https://doi.org/10.1016/j.bmcl.2010.09.052	journal	November 2010
A mechanistic analysis of the Rh-catalyzed intramolecular C–H amination reaction Fiori, Kristin Williams; Espino, Christine G.; Brodsky, Benjamin H. Tetrahedron, Vol. 65, Issue 16 https://doi.org/10.1016/j.tet.2008.11.073	journal	April 2009
Heterobimetallic Ir–Sn catalysis: aza-Friedel–Crafts reaction of N-sulfonyl aldimines Chatterjee, Paresh Nath; Maity, Arnab Kumar; Mohapatra, Swapna Sarita Tetrahedron, Vol. 69, Issue 13 https://doi.org/10.1016/j.tet.2013.01.074	journal	April 2013
Sulfonamidoglycosylation of methyl ribofuranosides: a novel approach to furanosylsulfonamides Colinas, Pedro A.; Bravo, Rodolfo D. Tetrahedron Letters, Vol. 46, Issue 10 https://doi.org/10.1016/j.tetlet.2005.01.065	journal	March 2005
Metal-free N-iodosuccinimide-catalyzed mild oxidative C–H bond amination of benzoxazoles Wagh, Yogesh S.; Sawant, Dinesh N.; Bhanage, Bhalchandra M. Tetrahedron Letters, Vol. 53, Issue 27 https://doi.org/10.1016/j.tetlet.2012.04.117	journal	July 2012
Metal-free synthesis of 2-aminobenzoxazoles using hypervalent iodine reagent Wagh, Yogesh S.; Tiwari, Neelam J.; Bhanage, Bhalchandra M. Tetrahedron Letters, Vol. 54, Issue 10 https://doi.org/10.1016/j.tetlet.2012.12.127	journal	March 2013
Metal-Catalyzed Nitrogen-Atom Transfer Methods for the Oxidation of Aliphatic C–H Bonds Roizen, Jennifer L.; Harvey, Mark Edwin; Du Bois, J. Accounts of Chemical Research, Vol. 45, Issue 6 https://doi.org/10.1021/ar200318q	journal	January 2012
Unraveling the Mysteries of Microwave Chemistry Using Silicon Carbide Reactor Technology Kappe, C. Oliver Accounts of Chemical Research, Vol. 46, Issue 7 https://doi.org/10.1021/ar300318c	journal	March 2013
Sodium Periodate as a Primary Oxidant for Water-Oxidation Catalysts Parent, Alexander R.; Brewster, Timothy P.; De Wolf, Wendy Inorganic Chemistry, Vol. 51, Issue 11 https://doi.org/10.1021/ic300154x	journal	May 2012
Synthesis, Structure, and Reaction of 1-Alkynyl(aryl)-λ ³ -bromanes Ochiai, Masahito; Nishi, Yoshio; Goto, Satoru Journal of the American Chemical Society, Vol. 125, Issue 50 https://doi.org/10.1021/ja038777q	journal	December 2003
N- Tosyloxycarbamates as a Source of Metal Nitrenes: Rhodium-Catalyzed C−H Insertion and Aziridination Reactions Lebel, Hélène; Huard, Kim; Lectard, Sylvain Journal of the American Chemical Society, Vol. 127, Issue 41 https://doi.org/10.1021/ja0552850	journal	October 2005
A New Type of Imido Group Donor: Synthesis and Characterization of Sulfonylimino-λ ³ -bromane that Acts as a Nitrenoid in the Aziridination of Olefins at Room Temperature under Metal-Free Conditions Ochiai, Masahito; Kaneaki, Takao; Tada, Norihiro Journal of the American Chemical Society, Vol. 129, Issue 43 https://doi.org/10.1021/ja075811i	journal	October 2007
Intermolecular Oxidative C–N Bond Formation under Metal-Free Conditions: Control of Chemoselectivity between Aryl sp ² and Benzylic sp ³ C–H Bond Imidation Kim, Hyun Jin; Kim, Jiyu; Cho, Seung Hwan Journal of the American Chemical Society, Vol. 133, Issue 41 https://doi.org/10.1021/ja207296y	journal	October 2011
Metal-Free Intermolecular Oxidative C–N Bond Formation via Tandem C–H and N–H Bond Functionalization Kantak, Abhishek A.; Potavathri, Shathaverdhan; Barham, Rose A. Journal of the American Chemical Society, Vol. 133, Issue 49 https://doi.org/10.1021/ja2087085	journal	December 2011
Iodine(III)-Mediated Intermolecular Allylic Amination under Metal-Free Conditions Souto, José A.; Zian, Debora; Muñiz, Kilian Journal of the American Chemical Society, Vol. 134, Issue 17 https://doi.org/10.1021/ja3013193	journal	April 2012
Metal-Free Iodine(III)-Promoted Direct Intermolecular C–H Amination Reactions of Acetylenes Souto, José A.; Becker, Peter; Iglesias, Álvaro Journal of the American Chemical Society, Vol. 134, Issue 37 https://doi.org/10.1021/ja306211q	journal	September 2012
Nonheme Iron-Mediated Amination of C(sp ³ )–H Bonds. Quinquepyridine-Supported Iron-Imide/Nitrene Intermediates by Experimental Studies and DFT Calculations Liu, Yungen; Guan, Xiangguo; Wong, Ella Lai-Ming Journal of the American Chemical Society, Vol. 135, Issue 19 https://doi.org/10.1021/ja3122526	journal	May 2013
Selective Monooxidation of Light Alkanes Using Chloride and Iodate Fortman, George C.; Boaz, Nicholas C.; Munz, Dominik Journal of the American Chemical Society, Vol. 136, Issue 23 https://doi.org/10.1021/ja502657g	journal	May 2014
Discovery, Modeling, and Human Pharmacokinetics of N -(2-Acetyl-4,6-dimethylphenyl)-3-(3,4-dimethylisoxazol-5-ylsulfamoyl)thiophene-2-carboxamide (TBC3711), a Second Generation, ET _A Selective, and Orally Bioavailable Endothelin Antagonist ¹ Wu, Chengde; Decker, E. Radford; Blok, Natalie Journal of Medicinal Chemistry, Vol. 47, Issue 8 https://doi.org/10.1021/jm030528p	journal	April 2004
Structure−Activity Relationship Studies on N ³ -Substituted Willardiine Derivatives Acting as AMPA or Kainate Receptor Antagonists Dolman, Nigel P.; More, Julia C. A.; Alt, Andrew Journal of Medicinal Chemistry, Vol. 49, Issue 8 https://doi.org/10.1021/jm051086f	journal	April 2006
Amidation of Unfunctionalized Hydrocarbons Catalyzed by Ruthenium Cyclic Amine or Bipyridine Complexes Au, Sze-Man; Huang, Jie-Sheng; Che, Chi-Ming The Journal of Organic Chemistry, Vol. 65, Issue 23 https://doi.org/10.1021/jo000881s	journal	November 2000
Friedel−Crafts Arylation Reactions of N -Sulfonyl Aldimines or Sulfonamidesulfones with Electron-Rich Arenes Catalyzed by FeCl ₃ ·6H ₂ O: Synthesis of Triarylmethanes and Bis-heteroarylarylmethanes Thirupathi, Ponnaboina; Soo Kim, Sung The Journal of Organic Chemistry, Vol. 75, Issue 15 https://doi.org/10.1021/jo1010137	journal	August 2010
Iodine-Catalyzed Amination of Benzoxazoles: A Metal-Free Route to 2-Aminobenzoxazoles under Mild Conditions Lamani, Manjunath; Prabhu, Kandikere Ramaiah The Journal of Organic Chemistry, Vol. 76, Issue 19 https://doi.org/10.1021/jo201402a	journal	October 2011
δ and α SP ³ C−H Bond Oxidation of Sulfonamides with PhI(OAc) ₂ /I ₂ under Metal-Free Conditions Fan, Renhua; Pu, Dongming; Wen, Fengqi The Journal of Organic Chemistry, Vol. 72, Issue 23 https://doi.org/10.1021/jo7016982	journal	November 2007
Inter- and Intramolecular Addition/Cyclizations of Sulfonamide Anions with Alkynyliodonium Triflates. Synthesis of Dihydropyrrole, Pyrrole, Indole, and Tosylenamide Heterocycles Feldman, Ken S.; Bruendl, Michelle M.; Schildknegt, Klaas The Journal of Organic Chemistry, Vol. 61, Issue 16 https://doi.org/10.1021/jo9605814	journal	January 1996
Study on Radical Amidation onto Aromatic Rings with (Diacyloxyiodo)arenes Togo, Hideo; Hoshina, Yoichiro; Muraki, Takahito The Journal of Organic Chemistry, Vol. 63, Issue 15 https://doi.org/10.1021/jo980450y	journal	July 1998
A Novel Sulfonamidoglycosylation of Glycals Colinas, Pedro A.; Bravo, Rodolfo D. Organic Letters, Vol. 5, Issue 23 https://doi.org/10.1021/ol035838g	journal	November 2003
α-Amidation of Cyclic Ethers Catalyzed by Simple Copper Salt and a Mild and Efficient Preparation Method for α,ϖ-Amino Alcohols He, Ling; Yu, Jing; Zhang, Ji Organic Letters, Vol. 9, Issue 12 https://doi.org/10.1021/ol070537i	journal	June 2007
Intramolecular Oxidative Diamination and Aminohydroxylation of Olefins under Metal-Free Conditions Kim, Hyun Jin; Cho, Seung Hwan; Chang, Sukbok Organic Letters, Vol. 14, Issue 6 https://doi.org/10.1021/ol300166q	journal	February 2012
Mild Metal-Free Sequential Dual Oxidative Amination of C(sp ³ )–H bonds: Efficient Synthesis of Imidazo[1,5- a ]pyridines Yan, Yizhe; Zhang, Yonghui; Zha, Zhenggen Organic Letters, Vol. 15, Issue 9 https://doi.org/10.1021/ol4008487	journal	April 2013
α-Amidation of Cyclic Ethers Catalyzed by Simple Copper Salt and a Mild and Efficient Preparation Method for α,ϖ-Amino Alcohols He, Ling; Yu, Jing; Zhang, Ji Organic Letters, Vol. 15, Issue 23 https://doi.org/10.1021/ol403356a	journal	November 2013
Transition-Metal-Free Intermolecular Amination of sp ³ C−H Bonds with Sulfonamides Fan, Renhua; Li, Weixun; Pu, Dongming Organic Letters, Vol. 11, Issue 6 https://doi.org/10.1021/ol900090f	journal	March 2009
Copper-Catalyzed sp ³ C–H Amination Gephart, Raymond T.; Warren, Timothy H. Organometallics, Vol. 31, Issue 22 https://doi.org/10.1021/om300840z	journal	August 2012
Oxidation of Dibenzyl Ethers by Dilute Nitric Acid Joshi, S. R.; Sawant, S. B.; Joshi, J. B. Organic Process Research & Development, Vol. 5, Issue 2 https://doi.org/10.1021/op000085o	journal	March 2001
Microwaves in organic synthesis. Thermal and non-thermal microwave effects de la Hoz, Antonio; Díaz-Ortiz, Ángel; Moreno, Andrés Chem. Soc. Rev., Vol. 34, Issue 2 https://doi.org/10.1039/B411438H	journal	January 2005
Recent advances in transition metal-catalyzed sp ³ C–H amination adjacent to double bonds and carbonyl groups Ramirez, Thomas A.; Zhao, Baoguo; Shi, Yian Chem. Soc. Rev., Vol. 41, Issue 2 https://doi.org/10.1039/C1CS15104E	journal	January 2012
Synthesis of benzosultams via an intramolecular sp ² C–H bond amination reaction of o-arylbenzenesulfonamides under metal-free conditions Li, Yuewen; Ding, Qiuping; Qiu, Guanyinsheng Org. Biomol. Chem., Vol. 12, Issue 1 https://doi.org/10.1039/C3OB41810C	journal	January 2014
n-Bu ₄ NI/TBHP-catalyzed direct amination of allylic and benzylic C(sp ³ )–H with anilines under metal-free conditions Zhang, Xusheng; Wang, Min; Li, Pinhua Chem. Commun., Vol. 50, Issue 59 https://doi.org/10.1039/C4CC01189A	journal	January 2014
Metal-free oxidative synthesis of quinazolinones via dual amination of sp ³ C–H bonds Zhao, Dan; Wang, Teng; Li, Jian-Xin Chem. Commun., Vol. 50, Issue 49 https://doi.org/10.1039/C4CC02648A	journal	January 2014
Amination of ethers using chloramine-T hydrate and a copper(i) catalyst Albone, David P.; Challenger, Stephen; Derrick, Andrew M. Organic & Biomolecular Chemistry, Vol. 3, Issue 1 https://doi.org/10.1039/b410883c	journal	January 2005
Catalytic C–H amination: recent progress and future directions Collet, Florence; Dodd, Robert H.; Dauban, Philippe Chemical Communications, Issue 34 https://doi.org/10.1039/b905820f	journal	January 2009
Construction of 3-oxyindoles via hypervalent iodine mediated tandem cyclization–acetoxylation of o-acyl anilines Sun, Yi; Fan, Renhua Chemical Communications, Vol. 46, Issue 36 https://doi.org/10.1039/c0cc01911a	journal	January 2010
Selective functionalisation of saturated C–H bonds with metalloporphyrin catalysts Che, Chi-Ming; Lo, Vanessa Kar-Yan; Zhou, Cong-Ying Chemical Society Reviews, Vol. 40, Issue 4 https://doi.org/10.1039/c0cs00142b	journal	January 2011
Direct acetoxylation and etherification of anilides using phenyliodine bis(trifluoroacetate) Liu, Huan; Wang, Xuemin; Gu, Yonghong Organic & Biomolecular Chemistry, Vol. 9, Issue 5 https://doi.org/10.1039/c0ob00749h	journal	January 2011
Metal-free α-CH amination of ethers with hypervalent sulfonylimino-λ3-bromane that acts as an active nitrenoid Ochiai, Masahito; Yamane, Shinichi; Hoque, Md. Mahbubul Chemical Communications, Vol. 48, Issue 43 https://doi.org/10.1039/c2cc31523h	journal	January 2012
Metal-free, highly efficient organocatalytic amination of benzylic C–H bonds Xue, Qicai; Xie, Jin; Li, Huamin Chemical Communications, Vol. 49, Issue 35 https://doi.org/10.1039/c3cc41558a	journal	January 2013
Advances in the Direct Amination of Azole C-H Bonds Zhang, Ming Synthesis, Vol. 2011, Issue 21 https://doi.org/10.1055/s-0030-1260231	journal	September 2011
Metal-Free Oxidative C-H Bond Amination at Ambient Temperature Samanta, Rajarshi; Antonchick, Andrey Synlett, Vol. 23, Issue 06 https://doi.org/10.1055/s-0031-1290531	journal	February 2012
An Efficient Oxidative Cross-Coupling Reaction between C-H and N-H Bonds; A Transition-Metal-Free Protocol at Room Temperature Wu, Yinuo; Kwong, Fuk; Li, Pengfei Synlett, Vol. 24, Issue 15 https://doi.org/10.1055/s-0033-1339447	journal	August 2013
Highly Regioselective Amination of Unactivated Alkanes by Hypervalent Sulfonylimino- 3-Bromane Ochiai, M.; Miyamoto, K.; Kaneaki, T. Science, Vol. 332, Issue 6028 https://doi.org/10.1126/science.1201686	journal	April 2011
Transition-metal-free Benzylic C–H Bond Intermolecular Amination Utilizing Chloramine-T and I ₂ Takeda, Youhei; Hayakawa, Junpei; Yano, Kazuki Chemistry Letters, Vol. 41, Issue 12 https://doi.org/10.1246/cl.2012.1672	journal	December 2012
Ruthenium Porphyrin Catalyzed Friedel–Crafts type Reaction of Arenes with Imines Kurahashi, Takuya; Matsubara, Seijiro; Terada, Takuma HETEROCYCLES, Vol. 85, Issue 10 https://doi.org/10.3987/COM-12-12556	journal	January 2012

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