1-(but-3-en-2-yloxy)-2-iodobenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(but-3-en-2-yloxy)-2-iodobenzene
• 英文别名: 1-But-3-en-2-yloxy-2-iodobenzene
• 化学式: C₁₀H₁₁IO
• 分子量: 274.101
• InChiKey: HFOIJEGXIUSPQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(but-3-en-2-yloxy)-2-iodobenzene 在 正丁基锂 、 异丙醇频哪醇硼酸酯 、 1,2-bis(bis(3,5-dimethylphenyl)phosphanyl)benzene 、 copper(I) bromide 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 13.0h， 生成 (3RS,2SR)-3-benzyl-2-methyl-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Diarylation of Alkenes by a Cu-Catalyzed Migratory Insertion/Cross-Coupling Cascade

  摘要：

  A strategy for the catalytic diarylation of alkenes is presented. The method involves the migratory insertion of alkenes into an Ar-Cu complex to generate a new C(sp(3))-Cu complex, which subsequently undergoes reaction with an aryl iodide to constitute a vicinal diarylation of an alkene. The method provides access to benzofuran- and indoline-containing products. Furthermore, highly diastereoselective examples are presented, allowing access to complex, stereochemically rich structures from simple alkene starting materials.

  DOI：

  10.1021/ja509056j

文献信息

• Copper-Catalyzed Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling
  作者：Surendra Thapa、Prakash Basnet、Ramesh Giri

  DOI：10.1021/jacs.7b01922

  日期：2017.4.26

  We present a strategy that difunctionalizes unactivated olefins in 1,2-positions with two carbon-based entities. This method utilizes alkyl/arylzinc reagents derived from olefin-tethered alkyl/aryl halides that undergo radical cyclization to generate C(sp3)-Cu complexes in situ, which are intercepted with aryl and heteroaryl iodides. A variety of (arylmethyl)carbo- and heterocycles (N, O) can be synthesized

  我们提出了一种策略，用两个碳基实体对 1,2 位的未活化烯烃进行双官能化。该方法利用衍生自烯烃系烷基/芳基卤化物的烷基/芳基锌试剂，这些烷基/芳基卤化物经过自由基环化以原位生成 C(sp3)-Cu 配合物，其被芳基和杂芳基碘化物拦截。使用这种新方法可以合成各种（芳甲基）碳环和杂环（N，O）。
• Sodium-Ketyl Radical Anions by Reverse Pinacol Reaction and Their Coupling with Iodoarenes
  作者：Xinjun Tang、Armido Studer

  DOI：10.1021/acs.orglett.6b02184

  日期：2016.9.2

  Transition-metal-free C–C bond formation between aryl iodides and pinacols is presented. Pinacols are readily transformed by deprotonation with NaH to their Na-pinacolates. C–C-bond homolysis at room temperature generates in situ the corresponding Na-ketyl radical anions which react with various aryl iodides in a homolytic aromatic substitution reaction to form tertiary Na-alcoholates. Protonation

  提出了在芳基碘化物和频哪醇之间无过渡金属的C–C键形成。薄荷醇很容易通过用NaH质子化而转化成其Na-pinacolates。室温下C–C键均质分解会原位生成相应的Na-酮基自由基阴离子，这些阴离子与各种芳基碘化物在均相芳族取代反应中反应，形成叔Na-醇盐。质子化最终以前所未有的方式提供了叔醇。
• Radical relay cyclization/C–C bond formation of allyloxy-tethered aryl iodides with quinoxalin-2(1<i>H</i>)-ones <i>via</i> polysulfide anion photocatalysis
  作者：Zhongyi Zhang、Yaqin Zhou、Jiehui Wang、Yicheng Zhang、Lei Wang、Jie Liu、Chao Zhou、Min Wang、Pinhua Li

  DOI：10.1039/d3ob01978k

  日期：——

  A visible-light-induced radical relay cyclization/C–C bond formation of quinoxalin-2(1H)-ones with allyloxy-tethered aryl iodides using polysulfide anions as a photocatalyst is described. This protocol allows efficient access to a variety of complicated molecules bearing both quinoxalin-2(1H)-one and 2,3-dihydrobenzofuran motifs in high yields under mild reaction conditions with a broad range of substrates

  描述了使用多硫阴离子作为光催化剂，可见光诱导的喹喔啉-2( 1H )-酮与烯丙氧基系芳基碘化物的自由基中继环化/C-C键形成。该协议允许在温和的反应条件下使用多种底物以高产率有效获取带有喹喔啉-2(1 H )-一和2,3-二氢苯并呋喃基序的各种复杂分子。
• Diarylation of Alkenes by a Cu-Catalyzed Migratory Insertion/Cross-Coupling Cascade
  作者：Wei You、M. Kevin Brown

  DOI：10.1021/ja509056j

  日期：2014.10.22

  A strategy for the catalytic diarylation of alkenes is presented. The method involves the migratory insertion of alkenes into an Ar-Cu complex to generate a new C(sp(3))-Cu complex, which subsequently undergoes reaction with an aryl iodide to constitute a vicinal diarylation of an alkene. The method provides access to benzofuran- and indoline-containing products. Furthermore, highly diastereoselective examples are presented, allowing access to complex, stereochemically rich structures from simple alkene starting materials.