Atomically precise ultrasmall copper cluster for room-temperature highly regioselective dehydrogenative coupling.

Jia, Teng; Li, Yi-Xin; Ma, Xiao-Hong; Zhang, Miao-Miao; Dong, Xi-Yan; Ai, Jie; Zang, Shuang-Quan · Nat Commun · 2023

basic_science · Level V

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Abstract

Three-component dehydrogenative coupling reactions represent important and practical methodologies for forging new C-N bonds and C-C bonds. Achieving highly all-in-one dehydrogenative coupling functionalization by a single catalytic system remains a great challenge. Herein, we develop a rigid-flexible-coupled copper cluster [Cu<sub>3</sub>(NHC)<sub>3</sub>(PF<sub>6</sub>)<sub>3</sub>] (Cu<sub>3</sub>NC<sup>(NHC)</sup>) using a tridentate N-heterocyclic carbene ligand. The shell ligand endows Cu<sub>3</sub>NC<sup>(NHC)</sup> with dual attributes, including rigidity and flexibility, to improve activity and stability. The Cu<sub>3</sub>NC<sup>(NHC)</sup> is applied to catalyze both highly all-in-one dehydrogenative coupling transformations. Mechanistic studies and density functional theory illustrate that the improved regioselectivity is derived from the low energy of ion pair with copper acetylide and endo-iminium ions and the low transition state, which originates from the unique physicochemical properties of the Cu<sub>3</sub>NC<sup>(NHC)</sup> catalyst. This work highlights the importance of N-heterocyclic carbene in the modification of copper clusters, providing a new design rule to protect cluster catalytic centers and enhance catalysis.