苯炔与联烯、膦酸酯或邻炔基苯甲醛肟反应的研究
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摘要
苯炔是一类重要的具有高度反应活性的有机合成中间体,因而苯炔化学是有机合成的一个重要课题,近年来,随着温和条件下苯炔制备新方法的发现,苯炔化学获得了巨大的发展,越来越受到化学家的关注。本论文的主要研究内容如下：
(1)对近几年苯炔参与的反应的研究进展作了综述。主要从苯炔的结构、制备和反应类型等方面进行介绍和讨论。
(2)发展了一种钯催化苯炔与联烯反应选择性合成菲类化合物的方法。发现在催化量的[(allyl)PdCl]2及P(o-tol)3的存在下,各种联烯,包括中间和末端联烯,都能与苯炔发生三聚共环化反应顺利地得到中等到好产率的相应菲衍生物。实验证明,反应的化学选择性决定于联烯的结构。
(3)研究了苯炔与β-羰基膦酸酯的亲核加成反应,发展了一种在温和条件下苯炔插入β-羰基膦酸酯选择性合成邻酰基苄基膦酸酯的方法。在氟化铯的存在下,以THF做溶剂,2-氧-丙基膦酸酯的碳-碳σ键选择性发生断裂,再与苯炔加成生成中等到好产率的2-酰基苄基膦酸酯。
(4)报道了一种在温和条件下AgOTf催化邻炔基苯甲醛肟串联亲电环化-[3+2]环加成反应制备稠杂环化合物的方法。本反应过程为：(a)邻炔基苯甲醛肟分子内亲电环化反应；(b)与苯炔的[3+2]环加成反应。反应在70℃的乙腈和四氢呋喃的混合溶剂中进行,能以中等收率得到目标产物,反应产物有望在药物合成领域获得应用。
Aryne chemistry is an important topic in organic chemistry because arynes are highly strained and kinetically unstable molecules emerging as valuable reactive intermediates in organic synthesis. Recently, many efficient methods have been developed on the basis of o-silyl aryltriflates because o-silyl aryltriflates could be readily prepared, and be converted into benzynes in situ under mild conditions, Therefore, aryne chemistry is being received more and more attentions.
1. Recent progress in the aryne involved reactions is summarized. We discussed detailedly the structure, the preparation, and the reaction types of benzyne.
2. Palladium-catalyzed cocyclotrimerization of allenes with arynes has been developed for selectively synthesizing phenanthrenes. In the presence of [(allyl)PdCl]2 and P(o-tol)3, a variety of allenes, including internal and terminal allenes, underwent the cocyclotrimerization with arynes to afford the corresponding phenanthrenes in moderate to good yields. The results showed the selectivity of the reaction based on allenes.
3. A mild method for selective synthesis of o-acylbenzylphosphonates has been developed by the reactions of arynes withβ-ketophosphonates. In the presence of CsF and THF, the carbon-carbonσ-bonds of 2-oxopropylphosphonates were selectively cleaved and added to arynes providing the corresponding 2-acylbenzylphosphonates in moderate to good yields.
4. A mild method for synthesis of condensed heterocyclic compounds has been developed by the AgOTf-catalyzed tandem cyclization-[3+2] cycloaddition reactions of 2-alkynylbenzaldoximes. The reaction may proceed via intramolecular electrophilic cyclization of 2-alkynylbenzaldximes and [3+2] cycloadditon reactions with arynes. In the mixture of THF and MeCN at 70℃, the reaction was conducted smoothly to afford the desired product in moderate yields, and the as-products have displayed great probabilities in the applications in the area of pharmaceutical materials.
(1)对近几年苯炔参与的反应的研究进展作了综述。主要从苯炔的结构、制备和反应类型等方面进行介绍和讨论。
(2)发展了一种钯催化苯炔与联烯反应选择性合成菲类化合物的方法。发现在催化量的[(allyl)PdCl]2及P(o-tol)3的存在下,各种联烯,包括中间和末端联烯,都能与苯炔发生三聚共环化反应顺利地得到中等到好产率的相应菲衍生物。实验证明,反应的化学选择性决定于联烯的结构。
(3)研究了苯炔与β-羰基膦酸酯的亲核加成反应,发展了一种在温和条件下苯炔插入β-羰基膦酸酯选择性合成邻酰基苄基膦酸酯的方法。在氟化铯的存在下,以THF做溶剂,2-氧-丙基膦酸酯的碳-碳σ键选择性发生断裂,再与苯炔加成生成中等到好产率的2-酰基苄基膦酸酯。
(4)报道了一种在温和条件下AgOTf催化邻炔基苯甲醛肟串联亲电环化-[3+2]环加成反应制备稠杂环化合物的方法。本反应过程为：(a)邻炔基苯甲醛肟分子内亲电环化反应；(b)与苯炔的[3+2]环加成反应。反应在70℃的乙腈和四氢呋喃的混合溶剂中进行,能以中等收率得到目标产物,反应产物有望在药物合成领域获得应用。
Aryne chemistry is an important topic in organic chemistry because arynes are highly strained and kinetically unstable molecules emerging as valuable reactive intermediates in organic synthesis. Recently, many efficient methods have been developed on the basis of o-silyl aryltriflates because o-silyl aryltriflates could be readily prepared, and be converted into benzynes in situ under mild conditions, Therefore, aryne chemistry is being received more and more attentions.
1. Recent progress in the aryne involved reactions is summarized. We discussed detailedly the structure, the preparation, and the reaction types of benzyne.
2. Palladium-catalyzed cocyclotrimerization of allenes with arynes has been developed for selectively synthesizing phenanthrenes. In the presence of [(allyl)PdCl]2 and P(o-tol)3, a variety of allenes, including internal and terminal allenes, underwent the cocyclotrimerization with arynes to afford the corresponding phenanthrenes in moderate to good yields. The results showed the selectivity of the reaction based on allenes.
3. A mild method for selective synthesis of o-acylbenzylphosphonates has been developed by the reactions of arynes withβ-ketophosphonates. In the presence of CsF and THF, the carbon-carbonσ-bonds of 2-oxopropylphosphonates were selectively cleaved and added to arynes providing the corresponding 2-acylbenzylphosphonates in moderate to good yields.
4. A mild method for synthesis of condensed heterocyclic compounds has been developed by the AgOTf-catalyzed tandem cyclization-[3+2] cycloaddition reactions of 2-alkynylbenzaldoximes. The reaction may proceed via intramolecular electrophilic cyclization of 2-alkynylbenzaldximes and [3+2] cycloadditon reactions with arynes. In the mixture of THF and MeCN at 70℃, the reaction was conducted smoothly to afford the desired product in moderate yields, and the as-products have displayed great probabilities in the applications in the area of pharmaceutical materials.
引文
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