Publications

INDEPENDENT PUBLICATIONS

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44. Wasa, M.; Mori, S.; Zhao, C.; Wang, Y.; ; Nathan, J. Late-Stage C(sp³)–H Functionalization of Bioactive Piperazines. ChemRxiv. 2025, DOI: 10.26434/chemrxiv-2025-xb7h2

43. Mori, S.; Zhao, C.; Wang, T.; Wang, Y.; Nishio, Y.; Disney, M. D.; Wasa, M.
Drug-Derived Tetrahydropyrazines for Late-Stage α– and β-Functionalization of Piperazine-Based Pharmaceuticals. Angew. Chem., Int. Ed., 2026, e6711809. DOI: 10.1002/anie.6711809

42. Chapman, M.; Dai, C.; Wang, Y.; Zhao, C.; Pham, Q.; Chatterjee, A.; Wasa, M.
B(C₆F₅)₃-Catalyzed Chemical Tagging of Bioactive N-Alkylamines through β-Amino C(sp³)–H Functionalization. Org. Lett., 2026, 28, 5316–5322. DOI: 10.1021/acs.orglett.6c01364

41. Wang, Y.; Zhao, C.; Wang, T.; Steele, A.; Joshi, M.; Mori, S.; Chatterjee, A.; Shen, B.; 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, 147, 43424–43437. DOI: 10.1021/jacs.5c11236

40. 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, 134685. DOI: 10.1016/j.tet.2025.134685
In honor of Professor Eric Jacobsen; 2024 Tetrahedron Prize for Creativity in Organic Chemistry.

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. DOI: 10.1021/jacs.3c00169

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, 12, e202300198. DOI: 10.1002/ajoc.202300198
Dedicated to Professor Keiji Maruoka on the occasion of his 70th birthday. 

37. Yesilcimen, A.; Jiang, N.-C.; Gottlieb, F. H.; 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. DOI: 10.1021/jacs.2c01656

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

35. Chang, Y.; Cao, M.; Chan, J. Z.; Zhao, C.; Wang, Y.; Yang, R.; Wasa, M.
Enantioselective Synthesis of N-Alkylamines through β-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. DOI: 10.1021/jacs.0c13200

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. DOI: 10.1021/jacs.0c08599

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. DOI: 10.1039/D0OB01678K
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 α-Deuteration of Bioactive Carbonyl Compounds with D₂O. Adv. Synth. Catal., 2020, 362, 360–364. DOI: 10.1002/adsc.201901419
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. DOI: 10.1021/jacs.9b08662

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. DOI: 10.1021/jacs.8b13757

29. Chan, J. Z.; Chang, Y.; Wasa, M.
B(C₆F₅)₃-Catalyzed C–H Alkylation of N-Alkylamines Using Silicon Enolates without External Oxidant. Org. Lett., 2019, 21, 984–988. DOI: 10.1021/acs.orglett.8b03959

28. Shang, M.; Chan, J. Z.; Cao, M.; Chang, 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, 10593–10601. DOI: 10.1021/jacs.8b06699

27. Shang, M.; Cao, M.; Wang, Q.; Wasa, M.
Enantioselective Direct Mannich-Type Reactions Catalyzed by Frustrated Lewis Acid/Brønsted Base Complexes. Angew. Chem., Int. Ed., 2017, 56, 13338–13341. DOI: 10.1002/anie.201706266

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, 95–98. DOI: 10.1021/jacs.6b11908

25. Chan, J. Z.; Yao, W.; Hastings, B. T.; Lok, C. K.; Wasa, M.
Direct Mannich-Type Reactions Promoted by Frustrated Lewis Acid/Brønsted Base Catalysts. Angew. Chem., Int. Ed., 2016, 55, 13877–13881. DOI: 10.1002/anie.201608583

PRIOR WORK

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24. Bendelsmith, A. J.; Kim, S. C.; 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, 11414–11419. DOI: 10.1021/jacs.9b05556

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, 8754–8786. DOI: 10.1021/acs.chemrev.6b00622

22. Liu, R. Y.; Wasa, M.; Jacobsen, E. N.
Asymmetric Synthesis of Tertiary α-Chloro Esters by Non-Covalent Catalysis. Tetrahedron Lett., 2015, 56, 3428–3430. DOI: 10.1016/j.tetlet.2015.01.124

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, 12872–12875. DOI: 10.1021/ja5075163

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, 8138–8142. DOI: 10.1021/ja504196j

19. Chan, K. S. L.; Wasa, M.; Chu, L.; Laforteza, B. N.; Miura, M.; Yu, J.-Q.
Ligand-Enabled Cross-Coupling of C(sp³)–H Bonds with Arylboron Reagents via Pd(II)/Pd(0) Catalysis. Nat. Chem., 2014, 6, 146–150. DOI: 10.1038/nchem.1836

18. Figg, T. M.; Wasa, M.; Yu, J.-Q.; Musaev, D. G.
Understanding the Reactivity of Pd(0)/PR₃-Catalyzed Intermolecular C(sp³)–H Bond Arylation. J. Am. Chem. Soc., 2013, 135, 14206–14214. DOI: 10.1021/ja4053416

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, 3387–3390. DOI: 10.1021/ja400648w

16. Wasa, M.; Chan, K. S. L.; Zhang, X.-G.; He, J.; Miura, M.; Yu, J.-Q.
Ligand-Enabled Methylene C(sp³)–H Bond Activation with a Pd(II) Catalyst. J. Am. Chem. Soc., 2012, 134, 18570–18572. DOI: 10.1021/ja309325e

15. Zhang, X.-G.; Dai, H.-X.; 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, 11948–11951. DOI: 10.1021/ja305259n

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, 788–802. DOI: 10.1021/ar200185g

12. Wasa, M.; Engle, K. M.; Lin, D. W.; Yoo, E. J.; Yu, J.-Q.
Pd(II)-Catalyzed Enantioselective C–H Activation of Cyclopropanes. J. Am. Chem. Soc., 2011, 133, 19598–19601. DOI: 10.1021/ja207607s

11. Wasa, M.; Chan, K. S. L.; Yu, J.-Q.
Pd(II)-Catalyzed Cross-Coupling of C(sp²)–H Bonds with Alkyl-, Aryl- and Vinyl-Boron Reagents via Pd(II)/Pd(0) Catalysis. Chem. Lett., 2011, 40, 1004–1006. DOI: 10.1246/cl.2011.1004

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, 9081–9084. DOI: 10.1002/anie.201102985

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, 17378–17380. DOI: 10.1021/ja108754f

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, 605–616. DOI: 10.1002/ijch.201000038

7. Wasa, M.; Engle, K. M.; Yu, J.-Q.
Pd(II)-Catalyzed Olefination of sp³ C–H Bonds. J. Am. Chem. Soc., 2010, 132, 3680–3681. DOI: 10.1021/ja1010866

6. Wasa, M.; Yu, J.-Q.
Amide-Directed Arylation of sp³ C–H Bonds Using Pd(II) and Pd(0) Catalysts. Tetrahedron, 2010, 66, 4811–4815. DOI: 10.1016/j.tet.2010.03.111

5. Wasa, M.; Worrell, B. T.; Yu, J.-Q.
Pd(0)/PR₃-Catalyzed Arylation of Nicotinic and Isonicotinic Acid Derivatives. Angew. Chem., Int. Ed., 2010, 49, 1275–1277. DOI: 10.1002/anie.200906104

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, 9886–9887. DOI: 10.1021/ja903573p

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, 14058–14059. DOI: 10.1021/ja807129e

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, 7190–7191. DOI: 10.1021/ja801355s

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, 5685–5688. DOI: 10.1021/ol0618858