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網站首頁/有機反應/烯烴的制備/烯烴交叉復分解反應
烯烴交叉復分解反應

烯烴交叉復分解反應是指兩種端基烯烴在Ru(II)-卡賓(Grubbs Catalyst)催化下,放出乙烯的烯烴復分解反應。從統(tǒng)計學來看,反應應該生成三種可能的幾何異構體,再加上每種異構體各有 E/Z構型,因此共有六種產物。

此反應的選擇性近期得到更進一步的研究,有各種反應實例表明不同反應活性的烯烴都能高產率和高選擇性的反應。

烯烴復分解反應,按照反應過程中分子骨架的變化,可以分為五種情況:開環(huán)復分解、開環(huán)復分解聚合、非環(huán)二烯復分解聚合、關環(huán)復分解以及交叉復分解反應。

在1990年代, Robert H.Grubbs發(fā)現了實用性非常高的催化劑。之后烯烴復分解反應成為有機合成化學里最常用的反應之一。

常見的催化劑:


反應機理:

引發(fā):


最新文獻:



Rate Enhanced Olefin Cross-Metathesis Reactions: The Copper Iodide Effect
K. Voigtritter, S. Ghorai, B. H. Lipshutz, J. Org. Chem.201176, 4697-4702.




Olefin Cross-Metathesis Reactions at Room Temperature Using the Nonionic Amphiphile “PTS”: Just Add Water
B. H. Lipshutz, G. T. Aquinaldo, S. Ghorai, K. Voigtritter, Org. Lett.200810, 1325-1328.




Increased Efficiency in Cross-Metathesis Reactions of Sterically Hindered Olefins
I. C. Stewart, C. J. Douglas, R. H. Grubbs, Org. Lett.200810, 441-444.




Acryloyl Chloride: An Excellent Substrate for Cross-Metathesis. A One-Pot Sequence for the Synthesis of Substituted α,β-Unsaturated Carbonyl Derivatives
L. Ferrié, S. Bouzbouz, J. Cossy, Org. Lett.200911, 5446-5448.




A Rapid and Simple Cleanup Procedure for Metathesis Reactions
B. R. Galan, K. P. Kalbarczyk, S. Szczepankiewicz, J. B. Keister, S. T. Diver, Org. Lett.20079, 1203-1206.




Regioselective Cross-Metathesis Reaction Induced by Steric Hindrance
S. BouzBouz, R. Simmons, J. Cossy, Org. Lett., 20046, 3465-3467.




An Efficient Synthesis of Nitroalkenes by Alkene Cross Metathesis: Facile Access to Small Ring Systems
G. P. Marsh, P. J. Parsons, C. McCarthy, X. G. Corniquet, Org. Lett.20079, 2613-2616.




Selective Synthesis of (2Z,4E)-Dienyl Esters by Ene-Diene Cross Metathesis
G. Moura-Letts, D. P. Curran, Org. Lett.20079, 5-8.




Advanced Fine-Tuning of Grubbs/Hoveyda Olefin Metathesis Catalysts: A Further Step toward an Optimum Balance between Antinomic Properties
M. Bieniek, R. Bujok, M. Cabaj, N. Lugan, G. Lavigne, D. Arlt, K. Grela, J. Am. Chem. Soc.2006128, 13652-13653.




A Good Bargain: An Inexpensive, Air-Stable Ruthenium Metathesis Catalyst Derived from α-Asarone
K. Grela, M. Kim, Eur. J. Org. Chem.2003, 963-966.




The facile preparation of alkenyl metathesis synthons
T. W. Baughman, J. C. Sworen, K. B. Wagener, Tetrahedron, 200460, 10943-10948.




Ruthenium-Catalyzed Tandem Olefin Metathesis-Oxidations
A. A. Scholte, M. H. An, M. L. Snapper, Org. Lett.20068, 4759-4762.




Ruthenium-Catalyzed Tandem Cross-Metathesis/Wittig Olefination: Generation of Conjugated Dienoic Esters from Terminal Olefins
R. P. Murelli, M. L. Snapper, Org. Lett.20079, 1749-1752.




Preparation of Aliphatic Ketones through a Ruthenium-Catalyzed Tandem Cross-Metathesis/Allylic Alcohol Isomerization
D. Finnegan, B. A. Seigal, M. L. Snapper, Org. Lett.20068, 2603-2606.




Heteroaromatic Synthesis via Olefin Cross-Metathesis: Entry to Polysubstituted Pyridines
T. J. Donohoe, J. A. Basutto, J. F. Bower, A. Rathi, Org. Lett.201113, 1036-1039.




Cross Metathesis of N-Allylamines and α,β-Unsaturated Carbonyl Compounds: A One-Pot Synthesis of Substituted Pyrroles
S. Shafi, M. K?dziorek, K. Grela, Synlett2011, 124-128.



參考文獻

一、https://www.organic-chemistry.org/namedreactions/cross-metathesis.shtm

二、化學空間: https://cn.chem-station.com/reactions/2014/01/%e7%83%af%e7%83%83%e5%a4%8d%e5%88%86%e8%a7%a3%e5%8f%8d%e5%ba%94%ef%bc%88olefin-metathesis%ef%bc%89.html



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