鈷金屬催化劑對於熊田耦合反應的催化應用

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鈷金屬催化劑對於熊田耦合反應的催化應用

Development of Cobalt Catalysts for Catalytic Kumada Couplings

唐魁謙 , Masters　　Advisor：梁蘭昌　　

繁體中文

熊田耦合反應；鈷金屬；長碳鏈間的耦合；鄰位多取代；室溫的條件； Kumada Couplings ； CoCl2-TMEDA ； Cobalt Catalysts ； N-heterocyclic carbene ； Csp3-Csp3 coupling ； tri-ortho-substituted biaryls

Abstract │ Reference (59) │ Altmetrics

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Abstract

1.	Cobalt(TMEDA)-Catalyzed Cross-coupling Reactions of Primary or Secondary Alkyl Halides with Alkyl and Aryl Grignard Reagents
A simple and convenient catalytic system (CoCl2-TMEDA) is found to couple primary and secondary alkyl halides with alkyl and aryl Grignard reagents. The results show that the Csp3-Csp3 coupling completed in 15 mins at room temperature in the absence of β-H elimination side product, and also exhibit high reactivity between alkyl halides and aryl Grignard reagents, and show no tolerance toward sensitive functional groups. The mechanism exploration depending on the reaction of radical clock substrate suggests that the reaction proceeds via the radical path.

2.	Cobalt-NHC catalyzed biaryl preparation
An efficient and high-yield cross-coupling methodology of (hetero)aryl halides with aryl Grignard reagents was developed with the employment of catalytic CoCl2 and N-heterocyclic carbene (NHC) under mild conditions. This catalysis allows for the synthesis of sterically congested tri-ortho-substituted biaryls and tolerates various functional groups.

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(2) Xi, Z.; Zhou, Y.; Chen, W. J. Org. Chem 2008, 73, 8497.
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(3) Wang, L.; Wang, Z.-X. Org. Lett .2007, 9, 4335.
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(5) Zhou, J.; Fu, G. C. J. Am. Chem. Soc.2003, 125, 12527.
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(6) Li, H. J.; Wang, L. Chem. Eur. J .2006, 2006, 5099.
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(9) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem. Int. Ed .2004, 43, 1132.
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