Metal-catalyzed domino process

Like multicomponent reaction, the domino process is yet another type of reaction that has high bond-forming efficiency and therefore suitable for creating the molecular complexities. We are particularly interested in the development of following two types of domino processes.

a) Pd°-catalyzed domino process terminated by CH-activation/functionalization step. See for example:

The domino process presented a rare example wherein a C(sp3)-H bond was activated by a C(sp3)-PdII function leading to the formation of a C(sp3)-C(sp3) bond.

b) PdII-catalyzed addition of two nucleophiles across the multiple bonds. See for example:

Selected publications:

  1. Budai, B.; Leclair, A., Wang, Q., Zhu, J. “Copper-Catalyzed 1,2-Methoxy Methoxycarbonylation of Alkenes with Methyl Formate”Angew. Chem. Int. Ed. 2019, 58, 10305-10309.
  2. Bao, X.; Wang, Q.; Zhu, J. “Copper-catalyzed remote C(sp3)-H azidation and dehydrogenative trifluoromethylation of benzohydrazides” Nature Communication, 2019, 10, 769.
  3. Bao, X.; Wang, Q.; Zhu, J. “Dual Photoredox/Copper Catalysis for the Remote C(sp3)-H Functionalization of Alcohols and Alkyl Halides Via N-Alkoxypyridinium Salts” Angew. Chem. Int. Ed. 2019, 58, 2139-2143
  4. Li, Z.; Q. Wang, J. Zhu, “Copper-Catalyzed Remote C(sp3)-H Arylation of Carboxamides and Sulfonamides” Angew. Chem. Int. Ed. 2018, 57, 13288-13292.
  5. Kong, W.; Wang, Q.; Zhu, J. “Palladium-Catalyzed Enantioselective Domino Heck/Intermolecular C-H Bond Functionalization: Development and Application to the Synthesis of (+)-Esermethole” J. Am. Chem. Soc. 2015, 137, 16028-16031.
  6. Bunescu, A.; Wang, Q.; Zhu, J. “Copper-catalyzed Cyanomethylation of Allylic Alcohols with Concomitant 1,2-Aryl Migration: Efficient Synthesis of Functionalized Ketones Bearing an α-Quaternary Center” Angew. Chem. Int. Ed. 2015, 54, 3132-3135.
  7. Tong, S.; Wang, Q.; Wang, M.-X.; Zhu, J. “Tuning the Reactivity of Isocyano Group: Synthesis of Imidazoles and Imidazoliums from Propargylamines and Isonitriles in the Presence of Multiple Catalysts” Angew. Chem. Int. Ed. 2015, 54, 1293-1297.
  8. Yao, B.; Wang, Q.; Zhu, J. “Pd(II)-Catalyzed Cyclizative Cross Coupling of ortho-Alkynylanilines with ortho-Alkynylbenzamides under Aerobic Conditions” Angew. Chem. Int. Ed. 2013, 52, 12992-12996.
  9. Piou, P.; Bunescu, A.; Wang, Q.; Neuville, L.; Zhu, J. “Pd-Catalyzed Through-Space Double C(sp3)-H and C(sp2)-H Bond Activation Via 1,4-Pd Migration of Transient C(sp3)-Pd(II) Intermediate: Efficient Synthesis of [3,4]-Fused Oxindoles” Angew. Chem. Int. Ed. 2013, 52, 12385-12389.
  10. Yao, B.; Wang, Q.; Zhu, J. “Palladium-Catalyzed Cyclizative Coupling of ortho-Alkynylanilines with Terminal Alkynes Under Aerobic Conditions: An Efficient Synthesis of 2,3-Disubstituted 3-Alkynylindoles” Angew. Chem. Int. Ed. 2012, 51, 12311-12315