烷基胺中氨基的取代反应
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摘要
取代反应是有机化学反应的重要类型之一,它的本质是断裂化学键同时形成新的化学键从而使有机分子中的原子或基团被其他原子或基团取代。通过断裂碳-杂键进而形成新的碳-碳键,碳-杂键或碳-氢键的研究一直是取代反应研究的重要领域。相对于碳-卤键,碳-氧键,碳-磷键等,由于烷基胺中sp3碳-氮键较大的键能和氨基较弱的离去能力,使得关于如何采用合适的条件来高效的经济的断裂烷基胺sp3碳-氮键,特别是对映选择性的断裂sp3碳-氮键,进而对氨基进行取代的研究仍然是有机化学方法学研究的重要挑战之一。本文采用过渡金属有机钯催化剂和手性磷酸催化剂,有效实现了烯丙基胺和磺酰基活化的苄基胺在酸性条件下的氨基的催化取代反应和对映选择性取代反应,极大扩展了烷基胺等含氮化合物作为合成中间体在有机合成中的应用。
本文首先报道了烯丙基一级胺作为一种新型的烯丙基亲电试剂参与的烯丙基化取代反应。相对于烯丙基卤,烯丙基酯,烯丙基碳酸酯,烯丙基磷酸酯和烯丙基醇等已报道的烯丙基亲电试剂,烯丙基一级胺作为烯丙基亲电试剂参与的过渡金属催化的烯丙基烷基化反应具有产率高,原子经济性高,区域选择性和立体选择性高,对水的容忍性好等优点,为合成多种非手性和手性的烯丙基化合物提供了新的有效的方法。
利用烯丙基一级胺为烯丙基亲电试剂,本文发展了钯催化的烯丙基一级胺和亚磺酸钠在廉价的硼酸活化下的氨基取代烯丙基化反应,高产率的合成了一系列烯丙基砜。产物均为烯丙基碳-碳双键为E式的α位取代产物,具有高的区域选择性和立体选择性。烯丙基化反应的副产物为低分子量的氨分子,具有高的原子经济性。
本文发展了钯催化的α-手性烯丙基一级胺和亚磺酸钠的手性转移烯丙基化反应。利用廉价的(+)-酒石酸通过手性拆分方便的大量的获得高光学纯度的α-手性烯丙基一级胺,然后以非手性的O,O-双齿配体为配体,在0.1mo1%的低催化量的钯催化下与亚磺酸钠发生手性转移烯丙基化反应,获得一系列高光学纯度的取代产物α-手性烯丙基砜。具有99%ee的α-手性烯丙基一级胺反应可得到具有高达98%ee的α-手性烯丙基砜,手性转移程度高。
本文发展了钯催化的烯丙基一级胺与次磷酸和烃基次膦酸的氨基取代烯丙基化反应,高产率高区域选择性和立体选择性的合成多种结构的单取代烯丙基次膦酸和双取代的烯丙基烃基次膦酸。反应中次磷酸和烃基次膦酸既是亲核试剂又是酸性活化剂,反应体系甚至不需要额外加入活化剂。反应对水容忍度高,可以直接使用次磷酸水溶液作为原料进行反应而不需要无水条件,方便经济。
同时,本文报道了手性磷酸催化的通过对映选择性的断裂磺酰基活化的sp3碳-氮键的N-(3-吲哚基亚甲基)磺酸胺衍生物与硫醇的取代反应。在5mo1%的联-2-萘酚衍生的手性磷酸催化下,N-(3-吲哚基亚甲基)磺酸胺衍生物与苄硫醇在0℃或室温下通过不对称断裂sp3碳-氮键的动力学拆分反应,高产率高对映选择性的获得高光学纯度的N-(3-吲哚基亚甲基)磺酸胺衍生物,反应条件温和。为高光学纯度的N-(3-吲哚基亚甲基)磺酸胺衍生物的合成提供了除亚胺与吲哚的不对称Friedel-CraRs反应以外的新途径,并且底物结构范围更广。同时通过动力学研究得出反应对于底物磺酰胺和催化剂磷酸是一级,对于苄硫醇是零级,证明了反应是通过SNl机制进行的。
Substitution reaction is one of important types of organic chemical reactions, nature of which are chemical bonds cleavage and formation. Substitution reaction cleavaging carbon-heteroatom bonds to form new carbon-carbon, carbon-heteroatom, carbon-hydrogen bonds are always the important research areas of organic chemistry. Because of the larger bonding energy of sp3C-N bond and the weaker leaving ability of N comparing with C-X, C-O and C-P bonds, the research of new method for cleavage or enantioselective cleavage of sp3C-N bond of alkylamine is still one of the challengs of organic synthetic methodology. In this dissertation, we present new efficient and economical reactions for cleavage or enantioselective cleavage of sp C-N bonds of allylamine and benzylamine catalyzed by palladium or phosphoric acid under acidic conditions. These studies significantly extend the applications of alkylamines as synthetic intermediates in organic synthesis.
First, we report primary allylic amine as a new type of allylic electrophile. In contrast with allylic halides, esters, carbonates, phosphates and alcohols, the transition metal-catalyzed allylation reactions of primary allylic amines with nucleophiles have high yield, high atom economy, high stereoselectivity and regioselectivity, and good tolerance of water. It provides new effective methods for synthesis of achiral and chiral allylic compounds.
A versatile method for the preparation of allylic sulfones via the reaction of primary allylic amines with sodium alkylsulfinates catalyzed by palladium complex catalysts has been developed with high atom economy. Asymmetric synthesis of allylic sulfones from a-chiral primary allylic amines is also achieved with high enantioselectivity by chirality transfer.
Palladium-catalyzed allylation of hypophosphorous acid or H-phosphinic acids with primary allylic amines has been developed. In the transformation, hypophosphorous acid works as both nucleophile and additive, no extra additive is required and the products are obtained in excellent yields. It is convenitent that aqueous solution of hypophosphorous acid is used directly as reactant.
Substitution reaction of N-(3-indoly)methylic sulfonamides with mercaptans via enantioselective sp3C-N bond cleavage catalyzed by chiral phosphoric acid has also been developed. In the presence of10mol%of a chiral phosphoric acid, a variety of racemic N-benzylic sulfonamides having N-(3-indolyl)methyl groups smoothly undergo kinetic resolution with benzyl thiol at0℃or at room temperature and the remaining sulfonamides are recovered in moderate to excellent yields and with excellent ee.
本文首先报道了烯丙基一级胺作为一种新型的烯丙基亲电试剂参与的烯丙基化取代反应。相对于烯丙基卤,烯丙基酯,烯丙基碳酸酯,烯丙基磷酸酯和烯丙基醇等已报道的烯丙基亲电试剂,烯丙基一级胺作为烯丙基亲电试剂参与的过渡金属催化的烯丙基烷基化反应具有产率高,原子经济性高,区域选择性和立体选择性高,对水的容忍性好等优点,为合成多种非手性和手性的烯丙基化合物提供了新的有效的方法。
利用烯丙基一级胺为烯丙基亲电试剂,本文发展了钯催化的烯丙基一级胺和亚磺酸钠在廉价的硼酸活化下的氨基取代烯丙基化反应,高产率的合成了一系列烯丙基砜。产物均为烯丙基碳-碳双键为E式的α位取代产物,具有高的区域选择性和立体选择性。烯丙基化反应的副产物为低分子量的氨分子,具有高的原子经济性。
本文发展了钯催化的α-手性烯丙基一级胺和亚磺酸钠的手性转移烯丙基化反应。利用廉价的(+)-酒石酸通过手性拆分方便的大量的获得高光学纯度的α-手性烯丙基一级胺,然后以非手性的O,O-双齿配体为配体,在0.1mo1%的低催化量的钯催化下与亚磺酸钠发生手性转移烯丙基化反应,获得一系列高光学纯度的取代产物α-手性烯丙基砜。具有99%ee的α-手性烯丙基一级胺反应可得到具有高达98%ee的α-手性烯丙基砜,手性转移程度高。
本文发展了钯催化的烯丙基一级胺与次磷酸和烃基次膦酸的氨基取代烯丙基化反应,高产率高区域选择性和立体选择性的合成多种结构的单取代烯丙基次膦酸和双取代的烯丙基烃基次膦酸。反应中次磷酸和烃基次膦酸既是亲核试剂又是酸性活化剂,反应体系甚至不需要额外加入活化剂。反应对水容忍度高,可以直接使用次磷酸水溶液作为原料进行反应而不需要无水条件,方便经济。
同时,本文报道了手性磷酸催化的通过对映选择性的断裂磺酰基活化的sp3碳-氮键的N-(3-吲哚基亚甲基)磺酸胺衍生物与硫醇的取代反应。在5mo1%的联-2-萘酚衍生的手性磷酸催化下,N-(3-吲哚基亚甲基)磺酸胺衍生物与苄硫醇在0℃或室温下通过不对称断裂sp3碳-氮键的动力学拆分反应,高产率高对映选择性的获得高光学纯度的N-(3-吲哚基亚甲基)磺酸胺衍生物,反应条件温和。为高光学纯度的N-(3-吲哚基亚甲基)磺酸胺衍生物的合成提供了除亚胺与吲哚的不对称Friedel-CraRs反应以外的新途径,并且底物结构范围更广。同时通过动力学研究得出反应对于底物磺酰胺和催化剂磷酸是一级,对于苄硫醇是零级,证明了反应是通过SNl机制进行的。
Substitution reaction is one of important types of organic chemical reactions, nature of which are chemical bonds cleavage and formation. Substitution reaction cleavaging carbon-heteroatom bonds to form new carbon-carbon, carbon-heteroatom, carbon-hydrogen bonds are always the important research areas of organic chemistry. Because of the larger bonding energy of sp3C-N bond and the weaker leaving ability of N comparing with C-X, C-O and C-P bonds, the research of new method for cleavage or enantioselective cleavage of sp3C-N bond of alkylamine is still one of the challengs of organic synthetic methodology. In this dissertation, we present new efficient and economical reactions for cleavage or enantioselective cleavage of sp C-N bonds of allylamine and benzylamine catalyzed by palladium or phosphoric acid under acidic conditions. These studies significantly extend the applications of alkylamines as synthetic intermediates in organic synthesis.
First, we report primary allylic amine as a new type of allylic electrophile. In contrast with allylic halides, esters, carbonates, phosphates and alcohols, the transition metal-catalyzed allylation reactions of primary allylic amines with nucleophiles have high yield, high atom economy, high stereoselectivity and regioselectivity, and good tolerance of water. It provides new effective methods for synthesis of achiral and chiral allylic compounds.
A versatile method for the preparation of allylic sulfones via the reaction of primary allylic amines with sodium alkylsulfinates catalyzed by palladium complex catalysts has been developed with high atom economy. Asymmetric synthesis of allylic sulfones from a-chiral primary allylic amines is also achieved with high enantioselectivity by chirality transfer.
Palladium-catalyzed allylation of hypophosphorous acid or H-phosphinic acids with primary allylic amines has been developed. In the transformation, hypophosphorous acid works as both nucleophile and additive, no extra additive is required and the products are obtained in excellent yields. It is convenitent that aqueous solution of hypophosphorous acid is used directly as reactant.
Substitution reaction of N-(3-indoly)methylic sulfonamides with mercaptans via enantioselective sp3C-N bond cleavage catalyzed by chiral phosphoric acid has also been developed. In the presence of10mol%of a chiral phosphoric acid, a variety of racemic N-benzylic sulfonamides having N-(3-indolyl)methyl groups smoothly undergo kinetic resolution with benzyl thiol at0℃or at room temperature and the remaining sulfonamides are recovered in moderate to excellent yields and with excellent ee.
引文
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