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  • 學位論文

鎳與鈷金屬錯合物催化有機硼試劑與共軛烯類及炔類的加成與環化反應

Nickel and Cobalt-Catalyzed Addition and Cyclization Reactions of Organoboronic Acids with α,β-Unsaturated Alkenes and Alkynes

指導教授 : 鄭建鴻

摘要


In this thesis, several new nickel and cobalt catalyzed coupling and cyclization of organoboronic acids with carbon carbon □-components are discussed in detail. For convenience and better clarity, the thesis is divided into five chapters. Chapter 1 describes the over view of synthetic and biological applications of organoboronic reagents. Chapters 2 and 3 demonstrate nickel and cobalt catalyzed Mizoroki Heck and Michael type addition of organoboronic acids to α,β-unsaturated alkenes. The possible reaction mechanisms of Mizoroki Heck and Michael type addition reactions are proposed. A cobalt-catalyzed addition reaction of organoboronic acids with alkynes is described in Chapter 4. Isolation of aryl-cobalt intermediate and correlative cobalt complexes strongly support the proposed mechanism. The annulations of ortho-functionalized arylboronic acids with alkynes for the synthesis of isocoumarin derivatives are presented in Chapter 5 along with the biological applications.

並列摘要


參考文獻


[2] K. Yoshida, T. Hayashi, in Boronic acids: preparation and applications in organic synthesis and medicine, (Ed.: D. G. Hall), Wiley-VCH, Weinheim, 2005.
[3] a) A. Suzuki, in Metal Catalyzed Cross-Coupling Reactions, (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998. Chapter 2, pp 49; b) Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.: E. Negishi), John Wiley & Sons, New York, 2002.
[4] P. B. Tripathy, D. S. Matteson, Synthesis, 1990, 200.
[6] H. R. Snyder, J. A. Kuck, J. R. Johnson, J. Am. Chem. Soc. 1938, 60, 105.
[7] D. S. Mattenson, Stereodirected Synthesis with Organoboranes, Springer, Berlin, 1995, pp 1.

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