A novel palladium-catalyzed decarbonylative annulation between phthalimides and arynes was well-established, affording phenanthridinone derivatives in moderate to good yields.
In this paper, a rhodium-catalyzed sequential twofold ortho-CÀ H functionalization of N-phenylbenzimidamide with internal alkyne is reported. The double CÀ H activations proved viable in a one-pot fashion with the assistance of C=N and CÀ N bonds, providing a series of benzimidazoisoquinolines with high levels of positional selectivity control. The operationally simple transformation showed high functional group compatibility and featured the cleavage of CÀ H bonds located on different a moiety of the N-phenylbenzimidamide substrates. Detailed mechanistic studies provided strong support for CÀ H bond cleavage on the N-phenyl ring to be preferential compared with CÀ H bond cleavage on C-phenyl ring. As a multifunctional catalytic platform, the rhodium catalyst conducted two independent and compatible catalytic cycles in one pot.
An efficient synthesis of 2,3‐fused pyridines through a HKUST‐1 (copper(II) 1,3,5‐benzenetricarboxylate) catalyzed sequential amination/annulation/aromatization reaction of carbonyl compounds and N‐propargylamine is presented herein. The reaction is not restricted to reactive ketones, wherein the five‐, six‐membered cyclic ketones and benzyl, aryl ketones show good reactivity with N‐propargylenamine, delivering pyridines in moderate to good yields. Under reaction conditions devoid of high temperature and expensive catalyst, this method exhibits broad tolerance of functional groups, including CN, alkyl, benzyl and methoxy moieties as well as unprotected phenolic hydroxy group. Additionally, the role of organic link for HKUST‐1 has been considered as a key parameter for this transformation.
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