Diastereodivergent Hydrosilylative Enyne Cyclization Catalyzed by N‐Heterocyclic Carbene‐Ni(0)

Main observation and conclusion Catalytic diastereodivergent hydrosilylative enyne cyclization with high generality and broad scope was achieved using electronic activated N‐heterocyclic carbene‐Ni(0) as a catalyst and R3SiH as silane (IPrCl, syn‐ : anti‐selectivity from up to 98 : 2 to 7 : 93 by Z...

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Bibliographic Details
Published in:Chinese journal of chemistry 2021-06, Vol.39 (6), p.1587-1592
Main Authors: Yu, Meng, Yong, Xuefeng, Gao, Weiwei, Ho, Chun‐Yu
Format: Article
Language:English
Subjects:
Alkynes
Catalysts
Diastereodivergent synthesis
Enynes
Hydroalkenylation
Hydrosilylation
N‐Heterocyclic carbenes
Selectivity
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Summary:Main observation and conclusion Catalytic diastereodivergent hydrosilylative enyne cyclization with high generality and broad scope was achieved using electronic activated N‐heterocyclic carbene‐Ni(0) as a catalyst and R3SiH as silane (IPrCl, syn‐ : anti‐selectivity from up to 98 : 2 to 7 : 93 by Z = O, NH vs. NMs, R1 = n‐pentyl). Heterocycles bearing homoallylsilane rather than vinylsilane was obtained chemoselectively. The undesired yet highly competitive reactivity was suppressed, like direct hydrosilylation of alkene and alkyne concurrently. Optionally, the homoallylsilane products could be reduced further in one‐pot using IPrMe as ligand and (EtO)3SiH as silane under otherwise the same standard condition as the above, offering practical access to additional stereocenters and more diverse product structures from enynes.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202000651