含硫化合物在生物化学、药物化学、功能材料等多个领域中有着广泛的应用，因此，发展C-S键高效构筑的新方法一直是有机合成化学研究的重要方向之一。

硫代磺酸酯是一类结构简单、廉价易得且性质稳定的有机硫化物，该类化合物同时含有硫基和磺酰基，通常被用来构建C-S键和C-SO₂键，是合成硫醚、亚砜以及砜类等有机硫化合物的重要试剂。近年来，随着“绿色可持续化学”的发展，开发条件温和、反应高效的有机硫化物的合成新方法已经成为有机合成化学的研究热点之一。本论文作者以硫代磺酸酯为硫化试剂，在温和反应条件下，发展了布朗斯特碱催化下高效合成硫醚、烯基砜等有机硫化物的新方法，并对其反应机理进行了探索。本论文主要工作如下：

第一部分作者发展了一种t-Bu-P₄催化硫代磺酸酯和三甲基（全氟苯基）硅烷的亲核取代反应，以23%~97%的收率制备了29种全氟苯基硫醚化合物。该方法表现出无需添加金属催化剂、反应条件温和等优点，为全氟苯基硫醚化合物的制备提供了一种新的合成方法。

第二部分作者发展了一种Cs₂CO₃催化硫代磺酸酯和炔酮化合物的硫砜基化反应，一步构建了C-S键和C-SO₂键，以28%~98%的收率制备了104种硫代乙烯基砜类化合物。该方法具有原料廉价易得、反应条件温和、底物普适性广、原子经济性高和立体选择性优异等特点。

第三部分作者研究了Cs₂CO₃催化硫代磺酸酯、2-萘酚和炔酮化合物的三组分反应，分别以32%~98%的收率和35%~99%的收率制备了25种2-萘酚硫醚化合物和44种乙烯基砜类化合物。该反应具有良好的底物普适性和优异的立体选择性，为“一锅法”同时合成了多种硫醚化合物和乙烯基砜类化合物提供了一种新策略。

第四部分作者研究了DBU催化硫代磺酸酯、炔酮和氘水的三组分反应，同时构建了C-D键和C-SO₂键，制备了23种氘代乙烯基砜类化合物。

本论文作者开发了碱催化硫代磺酸酯参与的C-S键形成反应，合成了全氟苯基硫醚、硫代乙烯基砜、氘代乙烯基砜等化合物。这些方法具有反应条件温和、底物普适性广、官能团兼容性好、优异的化学及立体选择性优点。

Sulfur-containing compounds have broad applications in many fields, such as biochemistry, medicinal chemistry, and functional materials. Therefore, the development of new methods for constructing C-S bonds has been a research in organic synthetic chemistry.

Thiosulfates are a class of organic sulfides with simple structure, cheap and easy to obtain, and stable properties. These compounds contain both sulfur and sulfonyl groups, which are usually used to construct C-S and C-SO₂ bonds, and are important reagents for the synthesis of organic sulfur compounds such as thioethers, sulfoxides, and sulfones. In recent years, with the development of “green and sustainable chemistry”, the development of new methods for the synthesis of organosulfur compounds under mild conditions and with high efficiency has become one of the hot topics in organic synthetic chemistry. In this thesis, author has developed a new method for the Brønsted base-catalyzed efficient synthesis of organosulfides such as thioethers and alkenyl sulfones under mild reaction conditions using thiosulfonates as sulfurizing reagents, and the reaction mechanism has been explored. The main work of this thesis is as follows:

In the first part of this thesis, the author developed a t-Bu-P₄-catalyzed nucleophilic substitution reaction of thiosulfonates and trimethyl (perfluorophenyl) silanes to prepare 29 perfluorophenyl sulfides in 23%~97% yields. This method showed the advantages of no use of metal catalysts and mild reaction condition, which provides a new synthetic method for the preparation of perfluorophenyl sulfides.

In the second part of this thesis, the author developed a Cs₂CO₃-catalyzed thiosulfonation reaction of thiosulfonates and ynones with one-step construction of C-S and C-SO₂ bonds to prepare 104 thio vinyl sulfones in 28%~98% yields. The method is characterized by cheap and easy availability of raw materials, mild reaction conditions, broad substrate universality, high atom economy and excellent stereoselectivity.

In the third part of this thesis, the author investigated the Cs₂CO₃-catalyzed three-component reaction of thiosulfonates, 2-naphthols and ynones to prepare 25 2-naphthol thioether compounds and 44 vinyl sulfones in 32%~98% and 35%~99% yields, respectively. The reaction has good substrate universality and excellent stereoselectivity, which provides a new strategy for the simultaneous synthesis of a variety of thioethers and vinyl sulfones by the "one-pot method".

In the fourth part of this thesis, the author investigated the DBU-catalyzed three-component reaction of thiosulfonates, ynones, and deuterium water with simultaneous construction of C-D and C-SO₂ bonds to prepare 23 deuterated vinyl sulfones.

In this thesis, several types of Brønsted bases catalyzed C-S bond construction reactions involving thiosulfonates have been developed. A variety of structurally diverse sulfur-containg products including perfluorophenyl sulfides, vinyl sulfone sulfides, thio vinyl sulfones and deuterovinyl sulfones have been prepared successfully. These methods present the advantages of mild reaction conditions, broad substrate scope, good functional compatibility and excellent chemo- and stero-selectivity.

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