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Synthesis of 1,2,3,6-tetrahydropyridines

Recent Literature

A palladium-catalyzed highly 6-endo-selective alkyl-Heck reaction of unactivated alkyl iodides provides efficient access to various 5-phenyl-1,2,3,6-tetrahydropyridine derivatives, which are important structural motifs for bioactive molecules. Mechanistic investigations reveal a hybrid palladium-radical process.
X. Dong, Y. Han, F. Yan, Q. Liu, P. Wang, K. Chen, Y. Li, Z. Zhao, Y. Dong, H. Liu, Org. Lett., 2016, 18, 3758-3761.

Acid-promoted condensations of N-[(Z)-3-iodoallyl]-aminoacetaldehydes and hydrazine hydrate followed by Pd-catalyzed asymmetric intramolecular hydrazone-type Heck reactions provide allylic diazenes that rapidly undergo stereospecific denitrogenative [1,5]-sigmatropic rearrangement, furnishing 3-substituted tetrahydropyridines with high enantioselectivity.
S. Yu, L. Zhou, S. Ye, X. Tong, J. Am. Chem. Soc., 2023, 145, 7621-7627.

The ion-paired Lewis acid [FeCl2]+[FeCl4]- generated by the in situ disproportionation of FeCl3 catalyzes an aza-Diels-Alder reaction of nonactivated dienes and imines.
R. Tomifuji, J. Maeda, T. Takahashi, T. Kurahashi, S. Matsubara, Org. Lett., 2018, 20, 7474-7477.

[Et3NH]+[BF4]- as an H-bond donor in a toluene/water/(CH2OH)2 biphasic system efficiently promotes a transition-metal catalyzed carbon-halogen reductive elimination at low temperature. This enables a series of Pd(0)-catalyzed carbohalogenation reactions, including an unprecedented asymmetric carbobromination in the presence of readily available ligands.
X. Chen, J. Zhao, M. Dong, N. Yang, J. Wang, Y. Zhang, K. Liu, X. Tong, J. Am. Chem. Soc., 2021, 143, 1924-1931.