Publications

INDEPENDENT PUBLICATIONS

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[43] Wang, Y.; Zhao, C.; Wang, T.; Steele, A.; Joshi, M.; Mori, S.; Shen, B.; Chatterjee, A.; Disney, M. D.; Wasa, M. Chemical Tagging of N-Alkylamine-Containing Natural Products and Pharmaceuticals through C(sp3)–H Functionalization. J. Am. Chem. Soc. 2025, DOI: 10.1021/jacs.5c11236. [Link]

[42] Wang, Y.; Zhao, C.; Wasa, M. Site-selective Alcoholysis of Oligopeptides through N-Alkylation of a Secondary Amide unit by Cooperative Catalysis. Tetrahedron. 2025, 183. [Link]

In honor of Professor Eric Jacobsen; 2024 Tetrahedron Prize for Creativity in Organic Chemistry.

[41] Wasa, M.; Mori, S.; Zhao, C.; Wang, Y.; Jackson, N. Late-Stage C(sp³)–H Functionalization of Bioactive Piperazines. ChemRxiv. 2025, DOI: 10.26434/chemrxiv-2025-xb7h2. [Link]

[40] Zhao, C.; Wang, Y.; Steele, A.; Mori, S.; Shen, B.; Wasa, M. Chemical Tagging of N-Alkylamine-Containing Natural Products and Pharmaceuticals through C(sp3)–H Functionalization. ChemRxiv. 2024, DOI: 10.26434/chemrxiv-2024-8fdhv. [Link]

[39] Zhao, C.; Wang, Y.; Pham, Q.; Dai, C.; Chatterjee, A.; Wasa, M. Chemical Tagging of Bioactive Amides by Cooperative Catalysis: Applications in the Syntheses of Drug Conjugates. J. Am. Chem. Soc. 2023, 145, 14233–14250. [Link]

[38] Dai, C.;^‡ Chapman, M.;^‡ Wasa, M. α-Alkylation of Mono-Carbonyl Compounds with N-Allylamines through Cooperative Actions of Lewis Acids and a Brønsted Base. Asian J. Org. Chem. 2023, DOI: 10.1002/ajoc.202300198.  [Link] 

Dedicated to Professor Keiji Maruoka on the occasion of his 70th birthday. 

[37] Yesilcimen, A.;^‡ Jiang, N.;^‡ Gottlieb, F.; Wasa, M. Enantioselective Organocopper-Catalyzed Hetero Diels–Alder Reaction through in Situ Oxidation of Ethers into Enol Ethers. J. Am. Chem. Soc. 2022, 144, 6173-6179. [Link]

[36] Wasa, M.; Yesilcimen, A. Enantioselective Cooperative Catalysis within Frustrated Lewis Pair Complexes. J. Synth. Org. Chem. Jpn. 2021, 79, 1065-1072. [Link]

[35] Chang, Y.;^‡ Cao, M.;^‡ Chang, J. Z.; Zhao, Y.; Wang, Y.; Wasa, M. Enantioselective Synthesis of N-Alkylamines through beta-Amino C–H Functionalization Promoted by Cooperative Actions of B(C₆F₅)₃ and a Chiral Lewis Acid Co-Catalyst. J. Am. Chem. Soc. 2021, 143, 2441-2455. [Link]

[34] Chan, J. Z.;^‡ Yesilcimen, A.;^‡ Cao, M.; Zhang, Y.; Zhang, B.; Wasa, M. Direct Conversion of N-Alkylamines to N-Propargylamines Through C–H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules. J. Am. Chem. Soc. 2020, 142, 16493-16505. [Link]

[33] Cao, M.; Yesilcimen, A.; Prasad, S.; Genova, J.; Myers, T.; Wasa, M. Sequential Conia-Ene-Type Cyclization and Negishi Coupling by Cooperative Functions of B(C₆F₅)₃, ZnI₂, Pd(PPh₃)₄ and an Amine. Org. Biomol. Chem. 2020, 18, 7090-7093 . [Link]

Invited manuscript (Editors: Professors Motomu Kanai and Matthias Beller) in the special issue on Hybrid Catalysis.

[32] Chang, Y.; Myers. T.; Wasa, M. B(C6F5)3-Catalyzed alpha-Deuteration of Bioactive Carbonyl Compounds with D2O. Adv. Synth. Catal. 2020, 362, 360-364. [Link]

Dedicated to Professor Eric N. Jacobsen on the occasion of his 60th birthday.

[31] Chang, Y.;‡ Yesilcimen, A.;‡ Cao, M.; Zhang, Y.; Zhang, B.; Chan, J. Z.; Wasa, M. Catalytic Deuterium Incorporation within Metabolically Stable β-Amino C–H Bonds of Drug Molecules. J. Am. Chem. Soc. 2019, 141, 14570-14575. [Link]

[30] Cao, M.; Yesilcimen, A.; Wasa, M. Enantioselective Conia-Ene-Type Cyclizations of Alkynyl Ketones through Cooperative Action of B(C6F5)3, N-Alkylamine and a Zn-Based Catalyst. J. Am. Chem. Soc. 2019, 141, 4199-4203. [Link]

[29] Chan, J. Z.‡; Chan, Y.‡; Wasa, M. B(C6F5)3-Catalyzed C–H Alkylation of N-Alkylamines Using Silicon Enolates without External Oxidant. Org. Lett. 2019, 21, 984. [Link]

[28] Shang, M.‡; Chan, J. Z.‡; Cao, M.; Chan, Y.; Wang, Q.; Cook, B.; Torker, S.; Wasa, M. C–H Functionalization of Amines via Alkene-Derived Nucleophiles through Cooperative Action of Chiral and Achiral Lewis Acid Catalysts: Applications in Enantioselective Synthesis. J. Am. Chem. Soc. 2018, 140, 10593. [Link]

[27] Shang, M.; Cao, M.; Wang, Q.; Wasa, M. Enantioselective Direct Mannich-Type Reaction Catalyzed by Frustrated Lewis Acid/Brønsted Base Complexes. Angew. Chem., Int. Ed. 2017, 56, 13338. [Link]

[26] Shang, M.; Wang, X.; Koo, S. M.; Youn, J.; Chan, J. Z.; Yao, W.; Hastings, B. T.; Wasa, M. Frustrated Lewis Acid/Brønsted Base Catalysts for Direct Enantioselective α-Amination of Carbonyl Compounds. J. Am. Chem. Soc. 2017, 139, 95. [Link]

[25] Chan, J. Z.; Yao, W.; Hastings, B. T.; Lok, C. K.; Wasa, M. Direct Mannich-Type Reactions Promoted by Frustrated Lewis Acid/Bronsted Base Catalysts. Angew. Chem., Int. Ed. 2016, 55, 13877.

PRIOR WORK

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[24] Bendelsmith, A. J.; Kim, S. H; Wasa, M.; Roche, S. P.; Jacobsen, E. N. Enantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis. J. Am. Chem. Soc. 2019, 141, 11414.

[23] He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.; Yu, J.-Q. Palladium-Catalyzed Transformations of Alkyl C–H Bonds. Chem. Rev. 2017, 117, 8754.

[22] Liu, R. Y.; Wasa, M.; Jacobsen, E. N. Asymmetric Synthesis of Tertiary α-Chloro Esters by Non-Covalent Catalysis. Tetrahedron Lett. 2015, 56, 3428.

[21] Wasa, M.; Liu, R. Y.; Roche, S. P.; Jacobsen, E. N. Asymmetric Mannich Synthesis of α-Amino Esters by Anion-Binding Catalysis. J. Am. Chem. Soc. 2014, 136, 12872.

[20] Xiao, K. -J.; Lin, D. W.; Miura, M.; Zhu, R. -Y.; Gong, W.; Wasa. M.; Yu, J. -Q. Palladium(II)-Catalyzed Enantioselective C(sp3)–H Activation Using a Chiral Hydroxamic Acid Ligand. J. Am. Chem. Soc. 2014, 136, 8138.

[19] Chan, K. S. L.; Wasa, M.; Chu, L.; Laforteza, B.; Miura, M.; Yu, J. -Q. Ligand-Enabled Cross-Coupling of C(sp3)–H Bonds with Arylboron Reagents via Pd(II)/Pd(0) Catalysis. Nature Chem. 2014, 6, 146.

[18] Figg, T. M.; Wasa, M.; Yu, J. -Q.; Musaev, J. Understanding the Reactivity of Pd(0)/PR3-Catalyzed Intermolecular C(sp3)–H Bond Arylation. J. Am. Chem. Soc. 2013, 135, 14206.

[17] He, J.; Wasa, M.; Chan, K. S. L.; Yu, J. -Q. Palladium(0)-Catalyzed Alkynylation of C(sp3)–H Bonds. J. Am. Chem. Soc. 2013, 135, 3387.

[16] Wasa, M.; Chan, K. S. L.; Zhang, X.-G.; Miura, M.; Yu, J. -Q. Ligand-Enabled Methylene C(sp3)–H Bond Activation with a Pd(II) Catalyst. J. Am. Chem. Soc. 2012, 134, 18570.

[15] Zhang, X.-G.; Dai, H.; Wasa, M.; Yu, J. -Q. Pd(II)-Catalyzed Ortho Trifluoromethylation of Arenes and Insights into the Coordination Mode of Acidic Amide Directing Groups. J. Am. Chem. Soc. 2012, 134, 11948.

[14] Wasa, M.; Chan, K. S. L.; Yu, J. -Q. in Asymmetric Synthesis – The Essentials II (Eds.: Christmann, M., Bräse, S.), Wiley-VCH, Weinheim, 2012, 267.

[13] Engle, K. M.; Mei, T. -S.; Wasa, M.; Yu, J. -Q. Weak Coordination as a Powerful Means for Developing Broadly Useful C–H Functionalization Reactions. Acc. Chem. Res. 2011, 45, 788.

[12] Wasa, M.; Engle, K. M.; Lin, D.; Yoo, E. J.; Yu, J. -Q. Pd(II)-Catalyzed Enantioselective C–H Activation of Cyclopropanes. J. Am. Chem. Soc. 2011, 133, 19598.

[11] Wasa, M.; Chan, K. S. L.; Yu, J. -Q. Pd(II)-catalyzed Cross-coupling of C(sp2)–H Bonds and Alkyl–, Aryl–, and Vinyl–Boron Reagents via Pd(II)/Pd(0) Catalysis. Chem. Lett. 2011, 40, 1004.

[10] Chan, K. S. L.; Wasa, M.; Wang, X.; Yu, J. -Q. Palladium(II)-Catalyzed Selective Monofluorination of Benzoic Acids Using a Practical Auxiliary: A Weak-Coordination Approach. Angew. Chem. Int. Ed. 2011, 50, 9081.

[9] Yoo, E. J.; Wasa, M.; Yu, J. -Q. Pd(II)-Catalyzed Carbonylation of C(sp3)−H Bonds: A New Entry to 1,4-Dicarbonyl Compounds. J. Am. Chem. Soc. 2010, 132, 17378.

[8] Wasa, M.; Engle, K. M.; Yu, J. -Q. Cross-Coupling of C(sp3)–H Bonds with Organometallic Reagents via Pd(II)/Pd(0) Catalysis. Isr. J. Chem. 2010, 50, 605.

[7] Wasa, M.; Engle, K. M.; Yu, J. -Q. Pd(II)-Catalyzed Olefination of sp3 C−H Bonds. J. Am. Chem. Soc. 2010, 132, 3680.

[6] Wasa, M.; Yu, J. -Q. Amide-Directed Arylation of sp3 C–H Bonds using Pd(II) and Pd(0) Catalysts. Tetrahedron 2010, 66, 4811.

[5] Wasa, M.; Worrell, B. W.; Yu, J. -Q. Pd(0)/PR3-Catalyzed Arylation of Nicotinic and Isonicotinic Acid Derivatives. Angew. Chem. Int. Ed. 2010, 49, 1275.

[4] Wasa, M.; Engle, K. M.; Yu, J. -Q. Pd(0)/PR3-Catalyzed Intermolecular Arylation of sp3 C−H Bonds. J. Am. Chem. Soc. 2009, 131, 9886.

[3] Wasa, M.; Yu, J. -Q. Synthesis of β-, γ-, and δ-Lactams via Pd(II)-Catalyzed C−H Activation Reactions. J. Am. Chem. Soc. 2008, 130, 14058.

[2] Wang, D. -H.; Wasa, M.; Giri, R.; Yu, J. -Q. Pd(II)-Catalyzed Cross-Coupling of sp3 C−H Bonds with sp2 and sp3 Boronic Acids Using Air as the Oxidant. J. Am. Chem. Soc. 2008, 130, 7190.

[1] Giri, R.; Wasa, M.; Breazzano, S. P.; Yu, J. -Q. Converting gem-Dimethyl Groups into Cyclopropanes via Pd-Catalyzed Sequential C−H Activation and Radical Cyclization. Org. Lett. 2006, 8, 5685.