The ambient temperature Ullmann reaction and its application to the total synthesis of (.+-.)-steganacin

Recent Advances on Construction of Pyrrolophenanthridone Skeleton

“…Ar, DMF, 120 o C, 15 1998 年, Tsuge 小组 [19] 以 7-溴吲哚 13 为起始原料采 用与 Lauk 小组 [18] 相似的策略合成 Hippadine (1, Scheme Ullmann 反应是构建联芳基母核的经典方法 [20] , 但 经典的 Ullmann 反应通常需要高温. 1980 年, Ziegler 小 组 [21] 报道采用正丁基锂活化溴苯后, 可以在 Cu(I)介导 下在室温中完成 Ullmann 反应. 1999 年, Harrowven 小 组 [22] 将此方法应用到吡咯并菲啶酮的构建中: 通过使 用与前文中 Sakamoto 小组 [8] 双(三氟乙酰氧基)碘苯(PIFA)介导的氧化偶联反应 是构建联芳基化合物的常用方法 [23] .…”

Three types of reactions with intramolecular five-membered ring compounds in organic synthesis

“…(21-1), many kinds of organic compounds 21-2 are synthesized by the reaction of cyclo-metalated products 21-1 with many kinds of substrates ZXm by carbonylations, alkenylations, alkynylations, acylations, isocyanations and Diels-Alder Reactions described above. The other reactions such as transmetalations, deuterations [89], Ullmann type coupling reactions [90][91][92], C-C coupling reactions [93], halogenations [94], oxidations [95], resolutions [96][97][98], ring expansion reactions by insertion reactions of carbenes [99], the ortho-silylations of Scheme 5. Scheme 6. benzylidene amines with palladium or platinum catalysts [100,101], the asymmetric hydrogenations of dehydroamino acid derivatives [102], and asymmetric hydro phosphination reactions with chiral N,N-dimethyl-1-naphthylamine [103], are also actually utilized for many kinds of organic syntheses.…”

Reductive Ullmann Coupling of Aryl Halides by Palladium Nanoparticles Supported on Cellulose, a Recoverable Heterogeneous Catalyst

“…The classical Ullmann reaction is restricted to electron-deficient aryl halides and is not effective for chloroarenes which are readily accessible in large scales compared to other haloarenes [11]. The recent trend was to perform this reaction under mild conditions with less sensitivity to water or air [12]. This has led to perform the Ullmann coupling variant, catalyzed by nickel or palladium [13].…”