Catalytic C−H Bond Functionalization with Palladium(II): Aerobic Oxidative Annulations of Indoles
Abstract

A palladium-catalyzed aerobic oxidative annulation of indoles is described. We have demonstrated that a variety of factors influence these cyclizations, and in particular the electronic nature of the pyridine ligand is crucial. It is also remarkable that these oxidative cyclizations can proceed in good yield despite background oxidative decomposition pathways, testament to the facile nature with which molecular oxygen can serve as the direct oxidant for Pd(0). We have also shown that the mechanism most likely involves initial indole palladation (formal C−H bond activation) followed by migratory insertion and β-hydrogen elimination.
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- Xiaoyu Chen, Corentin Antoine Baratay, Maddison Elizabeth Mark, Xinfang Xu, Philip Wai Hong Chan. Gold and Brønsted Acid Catalyzed Spirocyclization of 2- and 3-Indolyl-Tethered 1,4-Enyne Acetates to Spiro[4,n]alkyl[b]indoles. Organic Letters 2020, 22 (7) , 2849-2853. https://doi.org/10.1021/acs.orglett.0c00929
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- Long Wang, Brad P. Carrow. Oligothiophene Synthesis by a General C–H Activation Mechanism: Electrophilic Concerted Metalation–Deprotonation (eCMD). ACS Catalysis 2019, 9 (8) , 6821-6836. https://doi.org/10.1021/acscatal.9b01195
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- Asier Carral-Menoyo, Alexander Misol, Marcos Gómez-Redondo, Nuria Sotomayor, Esther Lete. Palladium(II)-Catalyzed Intramolecular C–H Alkenylation for the Synthesis of Chromanes. The Journal of Organic Chemistry 2019, 84 (4) , 2048-2060. https://doi.org/10.1021/acs.joc.8b03051
- Xuezhen Kou, Qihang Shao, Chenghao Ye, Guoqiang Yang, Wanbin Zhang. Asymmetric Aza-Wacker-Type Cyclization of N-Ts Hydrazine-Tethered Tetrasubstituted Olefins: Synthesis of Pyrazolines Bearing One Quaternary or Two Vicinal Stereocenters. Journal of the American Chemical Society 2018, 140 (24) , 7587-7597. https://doi.org/10.1021/jacs.8b02865
- Pablo J. Cabrera, Melissa Lee, Melanie S. Sanford. Second-Generation Palladium Catalyst System for Transannular C–H Functionalization of Azabicycloalkanes. Journal of the American Chemical Society 2018, 140 (16) , 5599-5606. https://doi.org/10.1021/jacs.8b02142
- Dian Wang, Adam B. Weinstein, Paul B. White, Shannon S. Stahl. Ligand-Promoted Palladium-Catalyzed Aerobic Oxidation Reactions. Chemical Reviews 2018, 118 (5) , 2636-2679. https://doi.org/10.1021/acs.chemrev.7b00334
- Yu-Feng Lin, Chi Fong, Wan-Ling Peng, Kuei-Chien Tang, Yi-En Liang, and Wen-Tai Li . Synthesis of 3-(2-Olefinbenzyl)-4H-chromen-4-one through Cyclobenzylation and Catalytic C–H Bond Functionalization Using Palladium(II). The Journal of Organic Chemistry 2017, 82 (20) , 10855-10865. https://doi.org/10.1021/acs.joc.7b01626
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- Bradley J. Gorsline, Long Wang, Peng Ren, and Brad P. Carrow . C–H Alkenylation of Heteroarenes: Mechanism, Rate, and Selectivity Changes Enabled by Thioether Ligands. Journal of the American Chemical Society 2017, 139 (28) , 9605-9614. https://doi.org/10.1021/jacs.7b03887
- Christopher G. Newton, Shou-Guo Wang, Caio C. Oliveira, and Nicolai Cramer . Catalytic Enantioselective Transformations Involving C–H Bond Cleavage by Transition-Metal Complexes. Chemical Reviews 2017, 117 (13) , 8908-8976. https://doi.org/10.1021/acs.chemrev.6b00692
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- Yadong Feng, Nian Tian, Yudong Li, Chunqi Jia, Xuening Li, Lianhui Wang, and Xiuling Cui . Construction of Fused Polyheterocycles through Sequential [4 + 2] and [3 + 2] Cycloadditions. Organic Letters 2017, 19 (7) , 1658-1661. https://doi.org/10.1021/acs.orglett.7b00452
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- Hendrik F. T. Klare, Alexander F. G. Goldberg, Douglas C. Duquette, and Brian M. Stoltz . Oxidative Fragmentations and Skeletal Rearrangements of Oxindole Derivatives. Organic Letters 2017, 19 (5) , 988-991. https://doi.org/10.1021/acs.orglett.6b03789
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- Erik Stempel and Tanja Gaich . Cyclohepta[b]indoles: A Privileged Structure Motif in Natural Products and Drug Design. Accounts of Chemical Research 2016, 49 (11) , 2390-2402. https://doi.org/10.1021/acs.accounts.6b00265
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- Seema Dhiman and S. S. V. Ramasastry . One-Pot Relay Gold(I) and Brønsted Acid Catalysis: Cyclopenta[b]annulation of Indoles via Hydroamination/Nazarov-Type Cyclization Cascade of Enynols. Organic Letters 2015, 17 (20) , 5116-5119. https://doi.org/10.1021/acs.orglett.5b02632
- Joydev K. Laha and Neetu Dayal . A Tandem Approach to Functionalized Carbazoles from Indoles via Two Successive Regioselective Oxidative Heck Reactions Followed by Thermal Electrocyclization. Organic Letters 2015, 17 (19) , 4742-4745. https://doi.org/10.1021/acs.orglett.5b02265
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- Richard P. Loach, Owen S. Fenton, Kazuma Amaike, Dustin S. Siegel, Erhan Ozkal, and Mohammad Movassaghi . C7-Derivatization of C3-Alkylindoles Including Tryptophans and Tryptamines. The Journal of Organic Chemistry 2014, 79 (22) , 11254-11263. https://doi.org/10.1021/jo502062z
- Thomas J. Osberger and M. Christina White . N-Boc Amines to Oxazolidinones via Pd(II)/Bis-sulfoxide/Brønsted Acid Co-Catalyzed Allylic C–H Oxidation. Journal of the American Chemical Society 2014, 136 (31) , 11176-11181. https://doi.org/10.1021/ja506036q
- Yan Zhang, Jing Zheng, and Sunliang Cui . Rh(III)-Catalyzed C–H Activation/Cyclization of Indoles and Pyrroles: Divergent Synthesis of Heterocycles. The Journal of Organic Chemistry 2014, 79 (14) , 6490-6500. https://doi.org/10.1021/jo500902n
- Vladimir A. D’yakonov, Ol’ga A. Trapeznikova, Armin de Meijere, and Usein M. Dzhemilev . Metal Complex Catalysis in the Synthesis of Spirocarbocycles. Chemical Reviews 2014, 114 (11) , 5775-5814. https://doi.org/10.1021/cr400291c
- Cheng-Hao Ying, Shao-Bai Yan, and Wei-Liang Duan . 2-Hydroxy-1,10-phenanthroline vs 1,10-Phenanthroline: Significant Ligand Acceleration Effects in the Palladium-Catalyzed Oxidative Heck Reaction of Arenes. Organic Letters 2014, 16 (2) , 500-503. https://doi.org/10.1021/ol4033804
- Laura Palacios, Maria Jose Artigas, Victor Polo, Fernando J. Lahoz, Ricardo Castarlenas, Jesús J. Pérez-Torrente, and Luis A. Oro . Hydroxo–Rhodium–N-Heterocyclic Carbene Complexes as Efficient Catalyst Precursors for Alkyne Hydrothiolation. ACS Catalysis 2013, 3 (12) , 2910-2919. https://doi.org/10.1021/cs400739y
- Ge Wu and Weiping Su . Regio- and Stereoselective Direct N-Alkenylation of Indoles via Pd-Catalyzed Aerobic Oxidation. Organic Letters 2013, 15 (20) , 5278-5281. https://doi.org/10.1021/ol402503z
- Keary M. Engle and Jin-Quan Yu . Developing Ligands for Palladium(II)-Catalyzed C–H Functionalization: Intimate Dialogue between Ligand and Substrate. The Journal of Organic Chemistry 2013, 78 (18) , 8927-8955. https://doi.org/10.1021/jo400159y
- Pieter Claes, Jan Jacobs, Bart Kesteleyn, Tuyen Nguyen Van, and Norbert De Kimpe . Palladium(II)-Catalyzed Synthesis of 2H,3′H-Spiro[benzofuran-3,2′-naphthoquinones]. The Journal of Organic Chemistry 2013, 78 (17) , 8330-8339. https://doi.org/10.1021/jo400852z
- Takuya Yokosaka, Hiroki Nakayama, Tetsuhiro Nemoto, and Yasumasa Hamada . Acid-promoted Cascade Cyclization to Produce Fused-polycyclic Indole Derivatives. Organic Letters 2013, 15 (12) , 2978-2981. https://doi.org/10.1021/ol401128h
- Parthasarathy Gandeepan and Chien-Hong Cheng . Pd-Catalyzed π-Chelation Assisted ortho-C–H Activation and Annulation of Allylarenes with Internal Alkynes. Organic Letters 2013, 15 (9) , 2084-2087. https://doi.org/10.1021/ol400792y
- Zhiyuan Chen, Beili Lu, Zhenhua Ding, Ke Gao, and Naohiko Yoshikai . α-Palladation of Imines as Entry to Dehydrogenative Heck Reaction: Aerobic Oxidative Cyclization of N-Allylimines to Pyrroles. Organic Letters 2013, 15 (8) , 1966-1969. https://doi.org/10.1021/ol400638q
- Sandeep R. Kandukuri and Martin Oestreich . Aerobic Palladium(II)-Catalyzed Dehydrogenation of Cyclohexene-1-carbonyl Indole Amides: An Indole-Directed Aromatization. The Journal of Organic Chemistry 2012, 77 (19) , 8750-8755. https://doi.org/10.1021/jo301088f
- Peng Zhao, Rui Niu, Fen Wang, Keli Han, and Xingwei Li . Rhodium(III)- and Ruthenium(II)-Catalyzed Olefination of Isoquinolones. Organic Letters 2012, 14 (16) , 4166-4169. https://doi.org/10.1021/ol3018352
- Bo Chen, Wu Fan, Guobi Chai, and Shengming Ma . Electronic Effect Directed Au(I)-Catalyzed Cyclic C2–H Bond Functionalization of 3-Allenylindoles. Organic Letters 2012, 14 (14) , 3616-3619. https://doi.org/10.1021/ol301408g
- Parthasarathy Gandeepan and Chien-Hong Cheng . Allylic Carbon–Carbon Double Bond Directed Pd-Catalyzed Oxidative ortho-Olefination of Arenes. Journal of the American Chemical Society 2012, 134 (13) , 5738-5741. https://doi.org/10.1021/ja300168m
- Mikko V. Leskinen, Kai-Tai Yip, Arto Valkonen, and Petri M. Pihko . Palladium-Catalyzed Dehydrogenative β′-Functionalization of β-Keto Esters with Indoles at Room Temperature. Journal of the American Chemical Society 2012, 134 (13) , 5750-5753. https://doi.org/10.1021/ja300684r
- Ryan D. Baxter, David Sale, Keary M. Engle, Jin-Quan Yu, and Donna G. Blackmond . Mechanistic Rationalization of Unusual Kinetics in Pd-Catalyzed C–H Olefination. Journal of the American Chemical Society 2012, 134 (10) , 4600-4606. https://doi.org/10.1021/ja207634t
- Zhan Lu and Shannon S. Stahl . Intramolecular Pd(II)-Catalyzed Aerobic Oxidative Amination of Alkenes: Synthesis of Six-Membered N-Heterocycles. Organic Letters 2012, 14 (5) , 1234-1237. https://doi.org/10.1021/ol300030w
- Keary M. Engle, Peter S. Thuy-Boun, Michael Dang, and Jin-Quan Yu . Ligand-Accelerated Cross-Coupling of C(sp2)–H Bonds with Arylboron Reagents. Journal of the American Chemical Society 2011, 133 (45) , 18183-18193. https://doi.org/10.1021/ja203978r
- Tuo Jiang, Andreas K. Å. Persson, and Jan-E. Bäckvall . Palladium-Catalyzed Oxidative Carbocyclization/Arylation of Enallenes. Organic Letters 2011, 13 (21) , 5838-5841. https://doi.org/10.1021/ol202451f
- Wenliang Wu and Weiping Su . Mild and Selective Ru-Catalyzed Formylation and Fe-Catalyzed Acylation of Free (N–H) Indoles Using Anilines as the Carbonyl Source. Journal of the American Chemical Society 2011, 133 (31) , 11924-11927. https://doi.org/10.1021/ja2048495
- Julia M. Stauber, Andrew L. Wadler, Curtis E. Moore, Arnold L. Rheingold, and Joshua S. Figueroa . Coordination Properties of 2,5-Dimesitylpyridine: An Encumbering and Versatile Ligand for Transition-Metal Chemistry. Inorganic Chemistry 2011, 50 (15) , 7309-7316. https://doi.org/10.1021/ic201205p
- Ming Yu, Zunjun Liang, Yongyong Wang, and Yuhong Zhang . Palladium(II)-Catalyzed Direct Alkenylation and Arylation of Arenes: Removable 2-Pyridylsulfinyl Group Assisted C–H Bond Activation. The Journal of Organic Chemistry 2011, 76 (12) , 4987-4994. https://doi.org/10.1021/jo200666z
- Nicolas Guimond, Serge I. Gorelsky, and Keith Fagnou . Rhodium(III)-Catalyzed Heterocycle Synthesis Using an Internal Oxidant: Improved Reactivity and Mechanistic Studies. Journal of the American Chemical Society 2011, 133 (16) , 6449-6457. https://doi.org/10.1021/ja201143v
- Kai-Tai Yip and Dan Yang . Pd(II)-Catalyzed Intramolecular Amidoarylation of Alkenes with Molecular Oxygen as Sole Oxidant. Organic Letters 2011, 13 (8) , 2134-2137. https://doi.org/10.1021/ol2006083
- Richard I. McDonald, Guosheng Liu, and Shannon S. Stahl . Palladium(II)-Catalyzed Alkene Functionalization via Nucleopalladation: Stereochemical Pathways and Enantioselective Catalytic Applications. Chemical Reviews 2011, 111 (4) , 2981-3019. https://doi.org/10.1021/cr100371y
- Xue Gong, Guoyong Song, Hong Zhang, and Xingwei Li . Palladium-Catalyzed Oxidative Cross-Coupling between Pyridine N-Oxides and Indoles. Organic Letters 2011, 13 (7) , 1766-1769. https://doi.org/10.1021/ol200306y
- Xianya Zhou, Jiaying Luo, Jing Liu, Shengming Peng, and Guo-Jun Deng . Pd-Catalyzed Desulfitative Heck Coupling with Dioxygen as the Terminal Oxidant. Organic Letters 2011, 13 (6) , 1432-1435. https://doi.org/10.1021/ol200101x
- Chang-Liang Sun, Bi-Jie Li, and Zhang-Jie Shi . Direct C−H Transformation via Iron Catalysis. Chemical Reviews 2011, 111 (3) , 1293-1314. https://doi.org/10.1021/cr100198w
- Charles S. Yeung and Vy M. Dong . Catalytic Dehydrogenative Cross-Coupling: Forming Carbon−Carbon Bonds by Oxidizing Two Carbon−Hydrogen Bonds. Chemical Reviews 2011, 111 (3) , 1215-1292. https://doi.org/10.1021/cr100280d
- Chen Zhu and J. R. Falck . N-Acylsulfonamide Assisted Tandem C−H Olefination/Annulation: Synthesis of Isoindolinones. Organic Letters 2011, 13 (5) , 1214-1217. https://doi.org/10.1021/ol200093f
- Xuan Ye, Guosheng Liu, Brian V. Popp, and Shannon S. Stahl . Mechanistic Studies of Wacker-Type Intramolecular Aerobic Oxidative Amination of Alkenes Catalyzed by Pd(OAc)2/Pyridine. The Journal of Organic Chemistry 2011, 76 (4) , 1031-1044. https://doi.org/10.1021/jo102338a
- Andy S. Tsai, Mikaël Brasse, Robert G. Bergman, and Jonathan A. Ellman. Rh(III)-Catalyzed Oxidative Coupling of Unactivated Alkenes via C−H Activation. Organic Letters 2011, 13 (3) , 540-542. https://doi.org/10.1021/ol102890k
- Fen Wang, Guoyong Song, and Xingwei Li. Rh(III)-Catalyzed Tandem Oxidative Olefination−Michael Reactions between Aryl Carboxamides and Alkenes. Organic Letters 2010, 12 (23) , 5430-5433. https://doi.org/10.1021/ol102241f
- Michael B. Johansen and Michael A. Kerr. Direct Functionalization of Indoles: Copper-Catalyzed Malonyl Carbenoid Insertions. Organic Letters 2010, 12 (21) , 4956-4959. https://doi.org/10.1021/ol1020948
- Stéphanie Jaegli, Jeremy Dufour, Hai-long Wei, Tiffany Piou, Xin-Hua Duan, Jean-Pierre Vors, Luc Neuville, and Jieping Zhu . Palladium-Catalyzed Carbo-Heterofunctionalization of Alkenes for the Synthesis of Oxindoles and Spirooxindoles. Organic Letters 2010, 12 (20) , 4498-4501. https://doi.org/10.1021/ol101778c
- Keary M. Engle, Dong-Hui Wang, and Jin-Quan Yu. Ligand-Accelerated C−H Activation Reactions: Evidence for a Switch of Mechanism. Journal of the American Chemical Society 2010, 132 (40) , 14137-14151. https://doi.org/10.1021/ja105044s
- Congyang Wang, Souvik Rakshit, and Frank Glorius. Palladium-Catalyzed Intermolecular Decarboxylative Coupling of 2-Phenylbenzoic Acids with Alkynes via C−H and C−C Bond Activation. Journal of the American Chemical Society 2010, 132 (40) , 14006-14008. https://doi.org/10.1021/ja106130r
- Yoichiro Kuninobu, Peng Yu, and Kazuhiko Takai. Rhenium-Catalyzed Diastereoselective Synthesis of Aminoindanes via the Insertion of Allenes into a C−H Bond. Organic Letters 2010, 12 (19) , 4274-4276. https://doi.org/10.1021/ol101627x
- Zhenhua Ding and Naohiko Yoshikai. Cobalt-Catalyzed Addition of Azoles to Alkynes. Organic Letters 2010, 12 (18) , 4180-4183. https://doi.org/10.1021/ol101777x
- Frederic W. Patureau and Frank Glorius. Rh Catalyzed Olefination and Vinylation of Unactivated Acetanilides. Journal of the American Chemical Society 2010, 132 (29) , 9982-9983. https://doi.org/10.1021/ja103834b
- Zhuangzhi Shi, Yuxin Cui and Ning Jiao. Synthesis of β- and γ-Carbolinones via Pd-Catalyzed Direct Dehydrogenative Annulation (DDA) of Indole-carboxamides with Alkynes Using Air as the Oxidant. Organic Letters 2010, 12 (13) , 2908-2911. https://doi.org/10.1021/ol1007839
- Yi Lu, Dong-Hui Wang, Keary M. Engle and Jin-Quan Yu. Pd(II)-Catalyzed Hydroxyl-Directed C−H Olefination Enabled by Monoprotected Amino Acid Ligands. Journal of the American Chemical Society 2010, 132 (16) , 5916-5921. https://doi.org/10.1021/ja101909t
- Xingang Zhang, Shilu Fan, Chun-Yang He, Xiaolong Wan, Qiao-Qiao Min, Jie Yang and Zhong-Xing Jiang. Pd(OAc)2 Catalyzed Olefination of Highly Electron-Deficient Perfluoroarenes. Journal of the American Chemical Society 2010, 132 (13) , 4506-4507. https://doi.org/10.1021/ja908434e
- Masayuki Wasa, Keary M. Engle and Jin-Quan Yu. Pd(II)-Catalyzed Olefination of sp3 C−H Bonds. Journal of the American Chemical Society 2010, 132 (11) , 3680-3681. https://doi.org/10.1021/ja1010866
- George A. Kraus and Haitao Guo. A Flexible Synthesis of 2,3-Disubstituted Indoles from Aminobenzyl Phosphonium Salts. A Direct Synthesis of Rutaecarpine. The Journal of Organic Chemistry 2009, 74 (15) , 5337-5341. https://doi.org/10.1021/jo900718g
- Xiuling Han and Xiyan Lu. Novel Palladium-Catalyzed Acyloxylation/Cyclization of 2-(3′-Alkenyl)indoles. Organic Letters 2009, 11 (11) , 2381-2384. https://doi.org/10.1021/ol9007348
- Kai-Tai Yip, Nian-Yong Zhu and Dan Yang. Palladium-Catalyzed Highly Diastereoselective Oxidative Cascade Cyclization Reactions. Organic Letters 2009, 11 (9) , 1911-1914. https://doi.org/10.1021/ol900355h
- Yang-Hui Zhang, Bing-Feng Shi and Jin-Quan Yu. Pd(II)-Catalyzed Olefination of Electron-Deficient Arenes Using 2,6-Dialkylpyridine Ligands. Journal of the American Chemical Society 2009, 131 (14) , 5072-5074. https://doi.org/10.1021/ja900327e
- Wangqing Kong, Jie Cui, Yihua Yu, Guofei Chen, Chunling Fu and Shengming Ma . PtCl4-Catalyzed Cyclization Reaction of β-Allenols in the Presence of Indoles. Organic Letters 2009, 11 (6) , 1213-1216. https://doi.org/10.1021/ol802838v
- Dylan B. England and Albert Padwa. Gold-Catalyzed Cycloisomerization of N-Propargylindole-2-carboxamides: Application toward the Synthesis of Lavendamycin Analogues. Organic Letters 2008, 10 (16) , 3631-3634. https://doi.org/10.1021/ol801385h
- Jared C. Lewis, Robert G. Bergman and Jonathan A. Ellman . Direct Functionalization of Nitrogen Heterocycles via Rh-Catalyzed C−H Bond Activation. Accounts of Chemical Research 2008, 41 (8) , 1013-1025. https://doi.org/10.1021/ar800042p
- George A. Kraus and Haitao Guo. One-Pot Synthesis of 2-Substituted Indoles from 2-Aminobenzyl Phosphonium Salts. A Formal Total Synthesis of Arcyriacyanin A. Organic Letters 2008, 10 (14) , 3061-3063. https://doi.org/10.1021/ol801034x
- Robert J. Phipps, Neil P. Grimster and Matthew J. Gaunt. Cu(II)-Catalyzed Direct and Site-Selective Arylation of Indoles Under Mild Conditions. Journal of the American Chemical Society 2008, 130 (26) , 8172-8174. https://doi.org/10.1021/ja801767s
- Gordon Brasche, Jorge García-Fortanet, and Stephen L. Buchwald. Twofold C−H Functionalization: Palladium-Catalyzed Ortho Arylation of Anilides. Organic Letters 2008, 10 (11) , 2207-2210. https://doi.org/10.1021/ol800619c
- Egle M. Beccalli,, Gianluigi Broggini,, Michela Martinelli, and, Silvia Sottocornola. C−C, C−O, C−N Bond Formation on sp2 Carbon by Pd(II)-Catalyzed Reactions Involving Oxidant Agents. Chemical Reviews 2007, 107 (11) , 5318-5365. https://doi.org/10.1021/cr068006f
- Shengming Ma,, Shichao Yu,, Zhihua Peng, and, Hao Guo. Palladium-Catalyzed Functionalization of Indoles with 2-Acetoxymethyl-Substituted Electron-Deficient Alkenes. The Journal of Organic Chemistry 2006, 71 (26) , 9865-9868. https://doi.org/10.1021/jo061546s
- Ravisekhara P. Reddy and, Huw M. L. Davies. Dirhodium Tetracarboxylates Derived from Adamantylglycine as Chiral Catalysts for Enantioselective C−H Aminations. Organic Letters 2006, 8 (22) , 5013-5016. https://doi.org/10.1021/ol061742l
- Elizabeth M. Beck,, Neil P. Grimster,, Richard Hatley, and, Matthew J. Gaunt. Mild Aerobic Oxidative Palladium (II) Catalyzed C−H Bond Functionalization: Regioselective and Switchable C−H Alkenylation and Annulation of Pyrroles. Journal of the American Chemical Society 2006, 128 (8) , 2528-2529. https://doi.org/10.1021/ja058141u
- Sean H. Wiedemann,, Jonathan A. Ellman, and, Robert G. Bergman. Rhodium-Catalyzed Direct C−H Addition of 3,4-Dihydroquinazolines to Alkenes and Their Use in the Total Synthesis of Vasicoline. The Journal of Organic Chemistry 2006, 71 (5) , 1969-1976. https://doi.org/10.1021/jo052345b
- Aidi Kong,, Xiuling Han, and, Xiyan Lu. Highly Efficient Construction of Benzene Ring in Carbazoles by Palladium-Catalyzed endo-Mode Oxidative Cyclization of 3-(3‘-Alkenyl)indoles. Organic Letters 2006, 8 (7) , 1339-1342. https://doi.org/10.1021/ol060039u
- Chae S. Yi and, Sang Young Yun. Scope and Mechanistic Study of the Ruthenium-Catalyzed ortho-C−H Bond Activation and Cyclization Reactions of Arylamines with Terminal Alkynes. Journal of the American Chemical Society 2005, 127 (48) , 17000-17006. https://doi.org/10.1021/ja055608s
- Kai-Tai Yip,, Jin-Heng Li,, On-Yi Lee, and, Dan Yang. Aerobic Oxidative Cyclization under Pd(II) Catalysis: A Regioselective Approach to Heterocycles. Organic Letters 2005, 7 (25) , 5717-5719. https://doi.org/10.1021/ol052529c
- T. Punniyamurthy,, Subbarayan Velusamy, and, Javed Iqbal. Recent Advances in Transition Metal Catalyzed Oxidation of Organic Substrates with Molecular Oxygen. Chemical Reviews 2005, 105 (6) , 2329-2364. https://doi.org/10.1021/cr050523v
- Chae S. Yi,, Sang Young Yun, and, Ilia A. Guzei. Catalytic Synthesis of Tricyclic Quinoline Derivatives from the Regioselective Hydroamination and C−H Bond Activation Reaction of Benzocyclic Amines and Alkynes. Journal of the American Chemical Society 2005, 127 (16) , 5782-5783. https://doi.org/10.1021/ja042318n
- Hua Qian,, Tao Pei, and, Ross A. Widenhoefer. Development, Scope, and Mechanism of the Palladium-Catalyzed Intramolecular Hydroalkylation of 3-Butenyl β-Diketones. Organometallics 2005, 24 (2) , 287-301. https://doi.org/10.1021/om049373p