现场修饰的维悌希试剂在有机合成中的应用
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摘要
鳞盐和膦酸酯作为Wittig或Wittig-Homer试剂前体在有机合成中有着重要应用。鏻盐通常是由卤代烃与三苯基膦或三烷基膦反应制得；膦酸酯通常由卤代烃与亚膦酸三酯反应得到。但是一些卤代烃由于官能团取代效应的影响难以得到,这就给相应的Wittig试剂的制备带来了困难,所以由简单易得的鏻盐或膦酸酯出发,通过方便易行的操作制备复杂的Wittig试剂前体具有一定的应用价值。本论文中我们由简单易得的原料现场得到了其他方法不易制备的Wittig试剂,并对其进行Wittig烯化反应研究,论文主要包括以下部分：
1、联烯有着很好的反应活性及选择性,炔丙基-联烯重排是非常有效的原位产生联烯的方法。我们由简单易得的炔丙基鳞盐经联烯异构化/电环化过程得到了其他方法较难制得的鳞盐,并利用该鏻盐一锅法合成了多取代的烯基苯及多取代的烯基萘类化合物。
2、炔丙基鳞盐在碱的促进下发生联烯异构化现场产生联烯鳞盐,该联烯鏻盐与负离子亲核试剂发生Michael加成反应原位产生新的Wittig试剂,继而与分子内的羰基发生Wittig反应得到烯化产物,该方法可简便地合成多取代的噻吩、吡咯及环戊烯类化合物。
3、进行了苯炔插入膦酸酯碳-碳σ键中的研究,苯炔可有效的插入β-酯基膦酸酯和p-酮基膦酸酯中,现场产生的新膦酸酯在碱的作用下与醛或酮反应可一锅法得到苯炔插入的烯化产物。该方法由简单易得的膦酸酯现场制备复杂的膦酸酯,并可一锅法得到芳基烯化产物。
Phosphonium salts and phosphonates are widely used in organic synthesis as the precursors of Wittig (Wittig-Horner) reagents. Generally, phosphonium salts are prepared via the reaction of a halide and triarylphosphine/trialkylphosphine; phosphonates are prepared via the reaction of a halide and trialkylphosphite. However, these protocols might encounter difficulty when the desired halide is not so readily available, because of the effect of the substituent. In these cases, highly functionalized phosphonium salts and phosphonates are not readily available. The functionalization of phosphonium salts or phosphonates may offer an efficient method to obtain complex phosphonium salts and phosphonates from simple, readily available starting materials. On the basis of the background, this dissertation focuses on the preparation and olefination of highly functionalized phosphonium salts and phosphonates from simple, readily available starting materials.
1. Allene-mediated reactions have attracted much attention by the organic community, and the propargyl-allenyl isomerization has been a useful and efficient method to afford allenes in situ. We have developed a sequence of propargyl-allenyl isomerizations and electrocyclizations for the functionalization of phosphonium salts via simple starting materials, which may provide an efficient one-pot synthesis of polysubstituted vinylbenzenes and naphthalenes.
2. We have developed a sequence of propargyl-allenyl isomerizations/michael addition and Wittig olefination from propargylic phosphonium salts, which may provide an efficient one-pot synthesis for polysubstituted thiophenes, pyrroles and cyclopentenes.
3. We have demonstrated that the carbon-carbon σ-bond of β-carbonyl phosphonates can readily be cleaved and added to the carbon-carbon triple bond of arynes under extremely mild conditions. The present insertion reaction provided the corresponding2-acylbenzylphosphonates from the simple phosphonates, which were directly used in a one-pot Horner-type olefination reaction.
1、联烯有着很好的反应活性及选择性,炔丙基-联烯重排是非常有效的原位产生联烯的方法。我们由简单易得的炔丙基鳞盐经联烯异构化/电环化过程得到了其他方法较难制得的鳞盐,并利用该鏻盐一锅法合成了多取代的烯基苯及多取代的烯基萘类化合物。
2、炔丙基鳞盐在碱的促进下发生联烯异构化现场产生联烯鳞盐,该联烯鏻盐与负离子亲核试剂发生Michael加成反应原位产生新的Wittig试剂,继而与分子内的羰基发生Wittig反应得到烯化产物,该方法可简便地合成多取代的噻吩、吡咯及环戊烯类化合物。
3、进行了苯炔插入膦酸酯碳-碳σ键中的研究,苯炔可有效的插入β-酯基膦酸酯和p-酮基膦酸酯中,现场产生的新膦酸酯在碱的作用下与醛或酮反应可一锅法得到苯炔插入的烯化产物。该方法由简单易得的膦酸酯现场制备复杂的膦酸酯,并可一锅法得到芳基烯化产物。
Phosphonium salts and phosphonates are widely used in organic synthesis as the precursors of Wittig (Wittig-Horner) reagents. Generally, phosphonium salts are prepared via the reaction of a halide and triarylphosphine/trialkylphosphine; phosphonates are prepared via the reaction of a halide and trialkylphosphite. However, these protocols might encounter difficulty when the desired halide is not so readily available, because of the effect of the substituent. In these cases, highly functionalized phosphonium salts and phosphonates are not readily available. The functionalization of phosphonium salts or phosphonates may offer an efficient method to obtain complex phosphonium salts and phosphonates from simple, readily available starting materials. On the basis of the background, this dissertation focuses on the preparation and olefination of highly functionalized phosphonium salts and phosphonates from simple, readily available starting materials.
1. Allene-mediated reactions have attracted much attention by the organic community, and the propargyl-allenyl isomerization has been a useful and efficient method to afford allenes in situ. We have developed a sequence of propargyl-allenyl isomerizations and electrocyclizations for the functionalization of phosphonium salts via simple starting materials, which may provide an efficient one-pot synthesis of polysubstituted vinylbenzenes and naphthalenes.
2. We have developed a sequence of propargyl-allenyl isomerizations/michael addition and Wittig olefination from propargylic phosphonium salts, which may provide an efficient one-pot synthesis for polysubstituted thiophenes, pyrroles and cyclopentenes.
3. We have demonstrated that the carbon-carbon σ-bond of β-carbonyl phosphonates can readily be cleaved and added to the carbon-carbon triple bond of arynes under extremely mild conditions. The present insertion reaction provided the corresponding2-acylbenzylphosphonates from the simple phosphonates, which were directly used in a one-pot Horner-type olefination reaction.
引文
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