戈爾德貝格反應
戈爾德貝格反應(Goldberg reaction)是用苯胺或芳基醯胺[1][2][3]代替酚進行的Ullmann二芳醚合成。由德國女化學家、弗里茨·烏爾曼的妻子伊爾瑪·戈爾德貝格[4]發現。
![利用戈爾德貝格反應合成芬那酸](http://images.weserv.nl/?url=//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/GoldbergReaction.svg/569px-GoldbergReaction.svg.png)
鄰溴苯乙酮與苯甲醯胺進行偶聯的產物,可以用作Camps環化反應的起始原料。[6]
![Buchwald醯胺化反應](http://images.weserv.nl/?url=//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/BuchwaldAmidationReaction.svg/600px-BuchwaldAmidationReaction.svg.png)
戈爾德貝格等報導了一種用從碘化亞銅和鄰二氮菲製備的催化劑介導的芳基碘化物和芳胺之間的烏爾曼型芳香胺化偶聯反應。富電子的芳基碘化物也能進行反應,因此這種方法可用於彌補布赫瓦爾德-哈特維希反應有些情況下不適用於富電子芳滷的缺點。[7]
參見
參考資料
- ^ Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. A General and Efficient Copper Catalyst for the Amidation of Aryl Halides and the N-Arylation of Nitrogen Heterocycles. J. Am. Chem. Soc.(Communication). 2001, 123 (31): 7727–7729. doi:10.1021/ja016226z.
- ^ Klapars, A.; Huang, X.; Buchwald, S. L. A General and Efficient Copper Catalyst for the Amidation of Aryl Halides. J. Am. Chem. Soc.(Article). 2002, 124 (25): 7421–7428. doi:10.1021/ja0260465.
- ^ Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. The Role of Chelating Diamine Ligands in the Goldberg Reaction: A Kinetic Study on the Copper-Catalyzed Amidation of Aryl Iodides. J. Am. Chem. Soc.(Communication). 2005, 127 (12): 4120–4121. doi:10.1021/ja050120c.
- ^ Iram Goldberg. Ueber Phenylirungen bei Gegenwart von Kupfer als Katalysator. Berichte der deutschen chemischen Gesellschaft. 1906, 39 (2): 1691–1692. doi:10.1002/cber.19060390298.
- ^ C. F. H. Allen and G. H. W. McKee (1943). "Acridone". Org. Synth.; Coll. Vol. 2: 15.
- ^ Jones, C. P.; Anderson, K. W.; Buchwald, S. L. Sequential Cu-Catalyzed Amidation-Base-Mediated Camps Cyclization: A Two-Step Synthesis of 2-Aryl-4-quinolones from o-Halophenones. J. Org. Chem. 2007, 72 (21): 7968–7973. doi:10.1021/jo701384n.
- ^ H.B. Goodbrand, Nan-Xing Hu. Ligand-Accelerated Catalysis of the Ullmann Condensation: Application to Hole Conducting Triarylamines. Journal of Organic Chemistry. 1999, 64: 670–674. doi:10.1021/jo981804o.