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Carbon-carbon bond cleavage and rearrangement of benzene by a trinuclear titanium hydride

机译：三核氢化钛对碳的碳-碳键裂解和重排

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摘要

The cleavage of carbon-carbon (C-C) bonds by transition metals is of great interest, especially as this transformation can be used to produce fuels and other industrially important chemicals from natural resources such as petroleum and biomass. Carbon-carbon bonds are quite stable and are consequently unreactive under many reaction conditions. In the industrial naphtha hydrocracking process, the aromatic carbon skeleton of benzene can be transformed to methylcy-clopentane and acyclic saturated hydrocarbons through C-Cbond cleavage and rearrangement on the surfaces of solid catalysts. However, these chemical transformations usually require high temperatures and are fairly non-selective. Microorganisms can degrade aromatic compounds under ambient conditions, but the mechanistic details are not known and are difficult to mimic. Several transition metal complexes have been reported to cleave C-C bonds in a selective fashion in special circumstances, such as relief of ring strain, formation of an aromatic system, chelation-assisted cyclometallation and β-carbon elimination. However, the cleavage of benzene by a transition metal complex has not been reported. Here we report the C-C bond cleavage and rearrangement of benzene by a trinuclear titanium poly-hydride complex. The benzene ring is transformed sequentially to a methylcyclopentenyl and a 2-methylpentenyl species through the cleavage of the aromatic carbon skeleton at the multi-titanium sites. Our results suggest that multinudear titanium hydrides could serve as a unique platform for the activation of aromatic molecules, and may facilitate the design of new catalysts for the transformation of inactive aromatics.
机译：过渡金属对碳-碳（C-C）键的裂解引起了极大的兴趣，尤其是因为这种转化可用于从石油和生物质等自然资源生产燃料和其他工业上重要的化学物质。碳-碳键相当稳定，因此在许多反应条件下都不反应。在工业石脑油加氢裂化过程中，苯的芳族碳骨架可通过C-键裂解和在固体催化剂表面重排而转化为甲基环戊烷和无环饱和烃。然而，这些化学转化通常需要高温并且是非选择性的。微生物可以在环境条件下降解芳香族化合物，但机理细节尚不清楚，难以模拟。据报道，在特殊情况下，几种过渡金属络合物可以选择性地裂解C-C键，例如减轻环应力，形成芳族体系，螯合辅助的环金属化和β-碳消除。然而，尚未报道过过渡金属络合物裂解苯。在这里，我们报告了三核钛多氢化物配合物对苯的C-C键裂解和重排。通过在多钛位点裂解芳族碳骨架，苯环依次转化为甲基环戊烯基和2-甲基戊烯基。我们的结果表明，多核氢化钛可作为活化芳族分子的独特平台，并可促进新型催化剂的设计，以用于惰性芳烃的转化。

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  • 来源
    《Nature》 |2014年第7515期|413-415|共3页
  • 作者

    Shaowei Hu; Takanori Shima; Zhaomin Hou;

  • 作者单位

    Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan;

    Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan, Organometallic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan;

    Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan, Organometallic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan;

  • 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);
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