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Transition metals in organic chemistry: From Suzuki cross-coupling to the Diels-Alder cycloaddition.

机译:有机化学中的过渡金属:从Suzuki交叉偶联到Diels-Alder环加成。

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摘要

This thesis is an investigation of the use of transition metals to catalyze organic reactions. In the first part of the thesis, Pd(0)-catalyzed Suzuki cross-coupling reactions between 2,3-dibromonorbornadiene and aryl boronic acids were explored as a means to generate symmetrical and unsymmetrical aryl substituted norbornadienes. Optimization of the reaction conditions were determined to be: Pd2(dba)3 (0.5 mol%), tBu 3P (1.4 mol%), CsF in THF. In general, electron-rich aryl boronic acids lead to high yielding Suzuki products while electron-deficient aryl boronic acids produced 2,3-diarylnorbornadienes in lower yields.; In the second part of the thesis, a cationic Rh(I) species generated in situ from [RhCl(COD)]2 (2.5 mol%) and AgSbF6 (5.0 mol%) in acetone was investigated as a catalyst for the Diels-Alder cycloaddition of alkynyl halides. The cationic Rh(I) species was shown to be a highly active catalytic species for the intramolecular [4+2] cycloaddition. The Diels-Alder cycloaddition occurred smoothly and was unaffected by the nature of the halide. The intermolecular Diels-Alder cycloaddition with internal alkynyl halides was not successful under the conditions described for the intramolecular variant.
机译:本文是对过渡金属催化有机反应的研究。在论文的第一部分中,探索了Pd(0)催化的2,3-二溴单降冰片二烯与芳基硼酸之间的Suzuki交叉偶联反应,以产生对称和不对称的芳基取代的降冰片二烯。确定反应条件的最优化为:Pd 2(dba)3(0.5mol%),tBu 3P(1.4mol%),CsF的THF溶液。通常,富含电子的芳基硼酸会导致高产量的铃木产品,而缺乏电子的芳基硼酸会以较低的产率产生2,3-二芳基降冰片二烯。在论文的第二部分中,研究了由[RhCl(COD)] 2(2.5 mol%)和AgSbF6(5.0 mol%)在丙酮中原位生成的阳离子Rh(I)作为Diels-Alder的催化剂炔基卤的环加成。阳离子Rh(I)物质被证明是分子内[4 + 2]环加成反应的高活性催化物质。 Diels-Alder环加成反应顺利进行,不受卤化物性质的影响。在针对分子内变体描述的条件下,使用内部炔基卤化物进行的分子间Diels-Alder环加成反应不成功。

著录项

  • 作者

    Yoo, Woo-Jin.;

  • 作者单位

    University of Guelph (Canada).;

  • 授予单位 University of Guelph (Canada).;
  • 学科 Chemistry Organic.
  • 学位 M.Sc.
  • 年度 2005
  • 页码 123 p.
  • 总页数 123
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;
  • 关键词

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