(R)-tert-butyl(methyl)(naphthalen-1-yl)phosphine borane | 951782-32-4

• 英文名称: (R)-tert-butyl(methyl)(naphthalen-1-yl)phosphine borane
• 英文别名: (R)-(+)-tert-butyl(methyl)-1-naphthylphosphine borane
• CAS: 951782-32-4
• 化学式: C₁₅H₂₂BP
• 分子量: 244.124
• InChiKey: QYAZLCFSHAGFAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  tert-butyl(naphthalen-1-yl)phosphine oxide 在 sodium tetrahydroborate 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.33h， 生成 (R)-tert-butyl(methyl)(naphthalen-1-yl)phosphine borane
  参考文献：
  名称：

  Bulky, Optically Active P-Stereogenic Phosphine–Boranes from Pure H-Menthylphosphinates

  摘要：

  The transformation of readily available pure-H-menthylphosphinates into chiral phosphinous acid-boranes permits the elaboration of bulky P-stereogenic secondary phosphine-boranes. Taking advantage of the synthetic potential of these compounds, a broad range of hindered P-chiral tertiary phosphine-boranes has been prepared with excellent enantiomeric excesses. The utility of bulky o-tolylphosphines was illustrated by the synthesis of a rare enantiopure phosphapalladacycle (S-P,S-P)-12.

  DOI：

  10.1021/ja2034816

文献信息

• Synthesis of <i>P</i>-chiral phosphine compounds by palladium-catalyzed C–P coupling reactions
  作者：Cuiying Wang、Chang-Duo Yue、Jia Yuan、Jia-Lian Zheng、Ying Zhang、Hong Yu、Jian Chen、Sixuan Meng、Yang Yu、Guang-Ao Yu、Chi-Ming Che

  DOI：10.1039/d0cc05340f

  日期：——

  An efficient C–P coupling reaction of enantiopure tert-butylmethylphosphine-boranes with aryl and heteroaryl halides is developed by using Pd(OAc)2/dppf as a catalyst, affording a series of (S) or (R)-P-chiral phosphines in moderate to high yields and with ee values up to 99% ee. Moreover, the reaction time could be reduced from 72 h to 6 h with increased ee values under microwave irradiation.

  一个高效的C-P耦合对映体纯的反应叔-butylmethylphosphine-硼烷与芳基和杂芳基卤化物，通过使用开发的Pd（OAC）2 / DPPF作为催化剂，得到的一系列（小号）或（- [R ）- P -手性膦中等至高产量，且ee值高达99％ee。此外，在微波辐射下，随着ee值的增加，反应时间可以从72 h减少到6 h。
• BOM-Phosphinite as an Electrophilic P-Stereogenic Transfer Reagent for the Synthesis of Bulky Phosphines: Synthesis of <i>tert</i>-Butyl(3,5-di-<i>tert</i>-butylphenyl)BisP*
  作者：Pep Rojo、Antoni Riera、Xavier Verdaguer

  DOI：10.1021/acs.orglett.1c01522

  日期：2021.6.18

  electrophilic P-stereogenic transfer reagent for the synthesis of bulky tertiary phosphines. The novel methodology relies on a one-pot deprotection/substitution on the trivalent phosphinite that takes place with very high stereospecificity. The potential of this strategy is demonstrated with the synthesis of a wide scope of tertiary phosphines in excellent enantiomeric excess. The methodology was applied to

  BOM-叔-butylmethylphosphinite硼烷为笨重叔膦的合成的有效电P-立体转移试剂。这种新颖的方法依赖于对三价次膦酸盐进行的一锅脱保护/取代，该方法具有非常高的立体特异性。该策略的潜力通过以极好的对映体过量合成范围广泛的叔膦来证明。该方法用于合成庞大的 P-立体异构 BisP* 配体类似物。