Rhodium-catalysed homo-coupling of terminal alkynes: divergent synthesis of bioactive 1,3-diynes and conjugated enediynes

C(sp)-C(sp) cross-coupling of terminal alkynes represents a robust tool for building biologically active 1,3-diynes although confronted with huge challenges regarding selectivity control. Herein, a unique rhodium-catalysed homo-coupling of aromatic terminal alkynes has been achieved, enabling divers...

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Bibliographic Details
Published in:New journal of chemistry 2024-04, Vol.48 (16), p.7517-7523
Main Authors: Xiao, Yijie, Lv, Lijie, Luo, Nanxuan, Zhao, Peirui, Chen, Yao, Luo, Zhangshun, Yin, Houhua, He, Yi, Nie, Shenyou
Format: Article
Language:English
Subjects:
Alkynes
Biocompatibility
Catalysis
Cross coupling
Enediynes
Functional groups
Rhodium
Substrates
Synthesis
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Summary:C(sp)-C(sp) cross-coupling of terminal alkynes represents a robust tool for building biologically active 1,3-diynes although confronted with huge challenges regarding selectivity control. Herein, a unique rhodium-catalysed homo-coupling of aromatic terminal alkynes has been achieved, enabling diversity-oriented synthesis (DOS) of 1,3-diynes and conjugated enediynes with high selectivity. Notably, both symmetrical and unsymmetrical 1,3-diynes have been prepared in good yields under mild reaction conditions with wide substrate scope and excellent functional group compatibility. Gratifyingly, further biological evaluation disclosed that the conjugated enediynes exhibited good inhibitory activities against several cancer cell lines. Moreover, 1,3-diyne 2a could effectively inhibit ferroptosis with sub-micromolar activity (EC 50 = 114 nM in HT-1080 cell). C(sp)-C(sp) cross-coupling of terminal alkynes represents a robust tool for building biologically active 1,3-diynes although confronted with huge challenges regarding selectivity control.
ISSN:1144-0546
1369-9261
DOI:10.1039/d4nj00366g