• 主题
高级搜索  >
历史搜索 清空历史
首页> 外文期刊>Journal of the American Chemical Society >Silicon-Carbon Bond Formation via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Unactivated Secondary and Tertiary Alkyl Electrophiles
【24h】

Silicon-Carbon Bond Formation via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Unactivated Secondary and Tertiary Alkyl Electrophiles

机译：通过镍催化的亲核硅与未活化的仲和叔烷基亲电试剂的镍催化交叉偶联形成硅碳键

获取原文
获取原文并翻译 | 示例
           
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

A wide array of cross-coupling methods for the formation of C-C bonds from unactivated alkyl electrophiles have been described in recent years. In contrast, progress in the development of methods for the construction of C-heteroatom bonds has lagged; for example, there have been no reports of metal-catalyzed cross-couplings of unactivated secondary or tertiary alkyl halides with silicon nucleophiles to form C-Si bonds. In this study, we address this challenge, establishing that a simple, commercially available nickel catalyst (NiBr_2·diglyme) can achieve couplings of alkyl bromides with nucleophilic silicon reagents under unusually mild conditions (e.g., -20 ℃); especially noteworthy is our ability to employ unactivated tertiary alkyl halides as electrophilic coupling partners, which is still relatively uncommon in the field of cross-coupling chemistry. Stereochemical, relative reactivity, and radical-trap studies are consistent with a homolytic pathway for C-X bond cleavage.
机译：近年来，已经描述了各种各样的由未活化的烷基亲电试剂形成C-C键的交叉偶联方法。相反，构建C-杂原子键的方法的进展落后。例如，没有报告未活化的仲或叔烷基卤化物与硅亲核试剂形成C-Si键的金属催化交叉偶联。在这项研究中，我们解决了这一挑战，确立了一种简单的市售镍催化剂（NiBr_2·diglyme）可以在异常温和的条件下（例如-20℃）实现烷基溴化物与亲核硅试剂的偶联。尤其值得一提的是，我们能够使用未活化的叔烷基卤化物作为亲电偶合剂，这在交叉偶合化学领域中仍然相对罕见。立体化学，相对反应性和自由基捕获研究与C-X键裂解的均质途径一致。

著录项

  • 来源
    《Journal of the American Chemical Society》 |2016年第20期|6404-6407|共4页
  • 作者

    Crystal K. Chu; Yufan Liang; Gregory C. Fu;

  • 作者单位

    Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States;

    Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States;

    Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类
  • 关键词

相似文献

  • 外文文献
  • 中文文献
  • 专利
获取原文

客服邮箱：kefu@zhangqiaokeyan.com

京公网安备：11010802029741号 ICP备案号：京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有

  • 客服微信

  • 服务号