bis(4-tert-butylphenyl)zinc | 1231206-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(4-tert-butylphenyl)zinc
• 英文别名: (4-tBuC6H4)2Zn
• CAS: 1231206-03-3
• 化学式: C₂₀H₂₆Zn
• 分子量: 331.816
• InChiKey: IAVAKWRVQQMEPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  N-苯基邻苯二甲酰亚胺 、 bis(4-tert-butylphenyl)zinc 在 bis(1,5-cyclooctadiene)nickel (0) 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以143 mg的产率得到3-(4-(tert-butyl)phenyl)-3-hydroxy-2-phenylisoindolin-1-one
  参考文献：
  名称：

  Nickel-Catalyzed Direct Addition of Diorganozinc Reagents to Phthalimides: Selective Formation of Gamma-Hydroxylactams

  摘要：

  The nickel-catalyzed addition of diorganozinc reagents to phthalimides proceeds with excellent selectivity to provide 3-substituted-3-hydroxyisoindolin-1-one products. These 3-hydroxy--lactams are produced cleanly in high yield with numerous examples of imide substitution and a broad range of diorganozinc reagents that are prepared and utilized without purification.

  DOI：

  10.1055/s-0033-1339890
• 作为产物：
  描述：

  4-叔丁基溴苯 、 zinc(II) chloride 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 bis(4-tert-butylphenyl)zinc
  参考文献：
  名称：

  Nickel-Catalyzed Direct Addition of Diorganozinc Reagents to Phthalimides: Selective Formation of Gamma-Hydroxylactams

  摘要：

  The nickel-catalyzed addition of diorganozinc reagents to phthalimides proceeds with excellent selectivity to provide 3-substituted-3-hydroxyisoindolin-1-one products. These 3-hydroxy--lactams are produced cleanly in high yield with numerous examples of imide substitution and a broad range of diorganozinc reagents that are prepared and utilized without purification.

  DOI：

  10.1055/s-0033-1339890

文献信息

• Exploiting Synergistic Effects in Organozinc Chemistry for Direct Stereoselective C‐Glycosylation Reactions at Room Temperature
  作者：Alberto Hernán‐Gómez、Samantha A. Orr、Marina Uzelac、Alan R. Kennedy、Santiago Barroso、Xavier Jusseau、Sébastien Lemaire、Vittorio Farina、Eva Hevia

  DOI：10.1002/anie.201805758

  日期：2018.8.13

  Pairing a range of bis(aryl) zinc reagents ZnAr2 with the stronger Lewis acidic [(ZnArF2)] (ArF=C6F5), enables highly stereoselective cross‐coupling between glycosyl bromides and ZnAr2 without the use of a transition metal. Reactions occur at room temperature with excellent levels of stereoselectivity, where ZnArF2 acts as a non‐coupling partner although its presence is crucial for the execution of

  将一系列双（芳基）锌试剂ZnAr 2与较强的路易斯酸性[（ZnAr F 2）]（Ar F = C 6 F 5）配对，可实现糖基溴化物与ZnAr 2之间高度立体选择性的交叉偶联，而无需使用过渡金属。反应在室温下以极好的立体选择性发生，其中ZnAr F 2充当非偶联配偶体，尽管它的存在对于执行C（sp 2）–C（sp 3）键的形成过程。机理研究发现两种锌试剂之间存在独特的协同关系，从而避免了对过渡金属催化或强制反应条件的需求。偶联成功的关键是避免使用相对于二芳基锌化合物（例如THF）的路易斯碱的溶剂。
• Lewis acid–base interactions between platinum(<scp>ii</scp>) diaryl complexes and bis(perfluorophenyl)zinc: strongly accelerated reductive elimination induced by a Z-type ligand
  作者：Allegra L. Liberman-Martin、Daniel S. Levine、Micah S. Ziegler、Robert G. Bergman、T. Don Tilley

  DOI：10.1039/c6cc02433e

  日期：——

  Z-type interactions between bis(perfluorophenyl)zinc and platinum(II) diaryl complexes supported by 1,10-phenanthroline (phen), 2,2[prime or minute]-bipyridine (bpy), and bis(dimethylphosphino)ethane (dmpe) ligands are reported.

  1,10-菲咯啉（phen），2,2 [伯或分钟]-联吡啶（bpy）和双（二甲基膦基）乙烷（dmpe）所支持的双（全氟苯基）锌与铂（II）二芳基配合物之间的Z型相互作用）配体的报道。
• Iron-Catalyzed, Directed Oxidative Arylation of Olefins with Organozinc and Grignard Reagents
  作者：Laurean Ilies、Jun Okabe、Naohiko Yoshikai、Eiichi Nakamura

  DOI：10.1021/ol1009448

  日期：2010.6.18

  Chelation-controlled arylation of olefins with organozinc or Grignard reagents proceeds in the presence of an iron catalyst, under mild conditions and typically without the need of external ligands, to afford substituted olefins in high yield and with complete regio- and stereocontrol.

  烯烃与有机锌或格氏试剂的螯合控制的芳基化反应在铁催化剂的存在下，在温和的条件下且通常不需要外部配体的情况下进行，从而以高收率和完全的区域和立体控制提供了取代的烯烃。
• Cobalt-Catalyzed Arylative Cyclization of Acetylenic Esters and Ketones with Arylzinc Reagents through 1,4-Cobalt Migration
  作者：Jianming Yan、Naohiko Yoshikai

  DOI：10.1021/acscatal.6b01039

  日期：2016.6.3

  reported a cobalt-catalyzed migratory arylzincation reaction of an alkyne that features alkenyl-to-aryl 1,4-cobalt migration and cobalt-to-zinc transmetalation as key steps. We report herein that the cobalt/arylzinc combination can also promote a cascade arylative cyclization reaction of alkynes bearing pendant ester or ketone moieties to afford benzo-fused cyclic ketone or alcohol products, respectively

  1,4-迁移的有机钯和有机or物种已被用于发展涉及远程C–H键活化的各种级联反应。最近，我们报道了以炔基到芳基1,4-钴迁移和钴到锌的过渡金属化为关键步骤的炔烃的钴催化迁移性芳基锌化反应。我们在本文中报道，钴/芳基锌的组合还可以促进带有侧链酯或酮部分的炔烃的级联芳基环化反应，以分别提供苯并稠合的环酮或醇产物。该反应被认为是通过将炔烃插入芳基钴物种，1，4-钴迁移以及向羰基的分子内有机钴加成而进行的。
• Nickel-Catalyzed Direct Addition of Diorganozinc Reagents to Phthalimides: Selective Formation of Gamma-Hydroxylactams
  作者：Jeffrey Johnson、Joseph Dennis、Catherine Calyore、Jessica Sjoholm、J. Lutz、Joseph Gair

  DOI：10.1055/s-0033-1339890

  日期：——

  The nickel-catalyzed addition of diorganozinc reagents to phthalimides proceeds with excellent selectivity to provide 3-substituted-3-hydroxyisoindolin-1-one products. These 3-hydroxy--lactams are produced cleanly in high yield with numerous examples of imide substitution and a broad range of diorganozinc reagents that are prepared and utilized without purification.