我們以前的工作發表過銅立方體可以催化芳基炔烴硼氫化反應。本研究嘗試使用氧化亞銅立方體，八面體和菱形十二面體作為類似的硼氫化反應的催化劑。使用這些具有相同總表面積的氧化亞銅奈米晶體進行活性比較，並添加苯乙炔，三苯基膦和雙聯頻哪醇硼酸酯在1,4-二噁烷中以在60℃下反應五小時，可以得到高產率，且具有100％（E）形式產物的選擇性。{110}-菱形十二面體催化該反應的效率最高，產率為99％，八面體為73％，立方體只有62％。接下來，使用最有效的氧化亞銅菱形十二面體用於廣泛範圍的芳烴炔烴硼氫化反應已經賦予良好的69至99％的優異產率。SEM圖像和PXRD圖顯示反應後晶體形態和組成並沒有變化。

Our previous work has shown that Cu cubes can catalyze aryl alkyne hydroboration reactions. This study attempts to use Cu2O cubes, octahedra, and rhombic dodecahedra as catalysts for similar hydroboration reactions. Using these Cu2O nanocrystals having the same total surface area for their activity comparison, and adding phenylacetylene, triphenylphosphine as base, and bis(pinacolato)diboron in 1,4-dioxane to perform the hydroboration reaction at 60 ºC for 5 h, 100% (E)-form products have been obtained with high yields. {110}-bound rhombic dodecahedra were the most efficient in catalyzing this reaction giving 99% yield, octahedra was 73%, and cubes only 62%. Next, use the most efficient Cu2O rhombic dodecahedra for a broad range of aromatic alkyne hydroboration reaction has given product good to excellent yields of 69 to 99%. SEM images and PXRD patterns show no change to the crystal morphology and composition after the reaction.

ABSTRACT II
ACKNOWLEDGEMENT III
LIST OF CONTENTS IV
LIST OF TABLES V
LIST OF FIGURES VI
LIST OF SCHEMES X
1.Introduction 1
1.1 Cuprous oxide and its application properties with specific facets 1
1.2 The studies of hydroboration reaction 6
1.3 Hydroboration mechanism 8
1.4 Isomers of hydroborated product 10
2. Motivation 12
3. Experimental Section 13
3.1 Chemicals 13
3.2 Synthesis of Cu2O Nanocrystals 13
3.3 Cu2O Nanocrystal-Catalyzed Hydroboration Reactions 16
3.4 Recyclability of the Hydroboration Reaction 16
3.5 Heterogeneous Catalysis Test 17
4. Instrumentation 17
5. Results and Discussion 18
6. Conclusion 31
7. References 32
Appendix 34

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