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金属催化合成呋喃衍生物的最新进展
其他题名Recent advances in meatal -mediated synthesis of substituted furans
李林涛; 麻生明
2000
发表期刊有机化学
ISSN0253-2786
卷号20期号:5页码:701-711
摘要综述了近几年来利用金属催化合成多取代呋喃的方法。 分两大类介绍: 一是通过对呋喃环进行结构改造, 即呋喃金属试剂在过渡金属催化下与卤化物或酰氯发生偶联反应得到, 或呋喃卤化物与金属试剂、烯烃、炔烃偶联得到; 二是以非环状化合物为前提进行呋喃环的构筑, 即在金属试剂催化下, 1,2-联烯基酮β-碘代β烯酮、叁键在α,β-、βγ-、γδ-的炔酮、 4-炔-2-烯醇可以关环得到多取代的呋喃产物。 此外,在Ru^2(Oac)^4催化下,α-叠氮酮与炔烃反应得到金属卡宾中间体, 然后关环也可得到取代呋喃产物。
其他摘要The regiospecific synthesis of substituted finns by metal - catalyzed methodologies is reviewed. The whole review consists two parts.(1) Methodologies based on prefonned furans Fumnyl metal reagents (M = Sn, B, Zn, Mn etc) undergo transition metal- catalyzed cross coupling reaction with mpnic halides or soyl chlorides to afford the substituted flarans. On the another hand, finnyl halides can also undergo ems coupling reaction with orgnoaneta]lic reagents or terntial alkynes to affoid flmctionalized finns. Under the catalysis ct Pd(O), flnnyl halides can also react with alkenes to produce alkenyl substituted furans. The C-H activation reaction of finns with RuH^2 (CO)PPH^3 directly produced flnanyl ruthenitun intermediates, which can further react with certain silylsubstituted 1- alkynes to afford 3- substituted finns. The C - H bond activation occurred regioapecifically the 3- positions.(2) Methodologies based on the cyclization reaction of acyclic compounds The most efficient way to synthesize finns is the cyclization of the corresponding acychc precumors, which provides the diversity, efficiency, and selectivity for the substituted finns synthesized.Under the catalysis of Ru(II) or Ag(I), 1,2-allenyl ketone can undergo cycloisotnerization to afforded 3 - unsub-sdtuted frrmns. Recently Pd(O) - catalyzed coupling - cyclization reactions of organic halides and 1,2- allenyl ketones were also developed to afford polysubstituted furans. The diversity of furan thus synthesized depends on the type of organic halides as well as the substitution patterms of 1,2- allenyl ketones. Under the catalysis of Pd complexes,β-iodo- β-enone can undergo oxidative addition- cyclization or dimerization reaction to produce furans. Under the catalysis of Pd, another type of acyclic starting material suitable for the synthesis of furan is alkynones, the carhon -carbon triple bond csn be located at α,β-,β,γ-andγ,δ-positions. Both cycloisomierization and two - component coupling - cyclization have been reported. (Z) -4-Alkyn-2- enol can also he cyclized to afford polysubstibited furans, Here, the hydroxyl group acts as a nucleophile to attack the transition metal - activated C-C triple bonds.The Rn^2(Oae)^4 - catalyzed reaction of α - diazo ketones with alkyne also provides an efficien rout route to fuan derivative. In this reaction the key intermediates are metal carbenes. Their intermolecular reaction with alkynes and the intramolecular reaction with α,β-unsaturated enones would form the furan skeletones.
学科领域金属有机化学
部门归属中国科学院上海有机化学研究所金属有机化学开放实验室
收录类别SCI
语种中文
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/11816
专题金属有机化学国家重点实验室
通讯作者麻生明
推荐引用方式
GB/T 7714
李林涛,麻生明. 金属催化合成呋喃衍生物的最新进展[J]. 有机化学,2000,20(5):701-711.
APA 李林涛,&麻生明.(2000).金属催化合成呋喃衍生物的最新进展.有机化学,20(5),701-711.
MLA 李林涛,et al."金属催化合成呋喃衍生物的最新进展".有机化学 20.5(2000):701-711.
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