Efficient macrocyclization facilitated by skeleton preorganization

Rong-Yao Xu; Xiu Liu; Guang Sun; Zhi-Yuan Zhang; Ming Dong; Liya Zhao; Si-Miao Zhang; Xi-Yang Wang; Hong-Xu Zhang; Shang-Jie Yang; Xiuguang Wang; Bin Li; Jian Li; Chunju Li

doi:10.1039/D3RA05671F

Efficient macrocyclization facilitated by skeleton preorganization†

Rong-Yao Xu,‡^a Xiu Liu,‡^a Guang Sun,‡^a Zhi-Yuan Zhang,

*^a Ming Dong,*^a Liya Zhao,^a Si-Miao Zhang,^a Xi-Yang Wang,^a Hong-Xu Zhang,^a Shang-Jie Yang,^a Xiuguang Wang,^a Bin Li,

^a Jian Li

^b and Chunju Li

*^a

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* Corresponding authors

^a Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, P. R. China
E-mail: zzy@tjnu.edu.cn, hxxydongm@tjnu.edu.cn, cjli@tjnu.edu.cn

^b School of Chemistry and Chemical Engineering, Henan Normal University, P. R. China

Abstract

Reported here is the efficient macrocyclization facilitated by skeleton preorganization. A pyridylcarbazole macrocycle and a phenylpyridylcarbazole macrocycle was synthesized in yield up to 75%. Single-crystal structures and theoretic computation uncovered that the skeleton preorganization promoted the formation of cyclization-favorable conformation of noncyclic precursors via π⋯π interactions. This result provided a new approach for the efficient syntheses of macrocycles.

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Efficient macrocyclization facilitated by skeleton preorganization†

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Efficient macrocyclization facilitated by skeleton preorganization

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