Palladium-Catalyzed Sequential Assembly of Nucleophilic Lactone-Embedded Benzofulvenes with π–Allylic Species and Nucleophiles

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC
Yang Li, Yan-Ping Lu, Xin-Han Yang, Tian-Ci Jie, Peng Shen, Chunyu Xia* and Guang-Yao Ran*, 
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引用次数: 0

Abstract

Compared with previously electrophilic benzofulvenes with exclusive reaction regioselectivity of the exocyclic double bond, novel lactone-embedded benzofulvenes with nucleophilicity and unique chemical properties have been designed and utilized in palladium-catalyzed sequential assembly with π-allylic species and various nucleophiles (including methoxide anion, alcohols, anilines, and alkylamines) through an unprecedented tandem allylation/ester bond cleavage process probably via a key oxocarbenium ion. The protocol featured high chemoselectivity and regioselectivity, constructing an array of densely functionalized indenes in high yields. Furthermore, the biological evaluation revealed that the synthesized indenes exhibited antitumor activity.

Abstract Image

钯催化的亲核内酯包埋苯并呋喃烷与π -烯丙基和亲核试剂的序贯组装
与以往具有外环双键独占反应区域选择性的亲电性苯并呋喃烷相比,设计了具有亲核性和独特化学性质的新型内酯包埋苯并呋喃烷,并将其用于钯催化下与π-烯丙基基团和各种亲核试剂(包括甲氧基阴离子、醇类、苯胺类、苯胺类、苯胺类)的序列组装。和烷基胺)通过前所未有的串联烯丙基化/酯键裂解过程,可能是通过一个关键的氧羰基离子。该方案具有高化学选择性和区域选择性,以高收率构建密集功能化的索引阵列。生物学评价表明,所合成的基因具有抗肿瘤活性。
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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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