有机碱催化贫电子炔的若干反应研究
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摘要
本文研究了以有机碱为催化剂催化贫电子炔的若干反应,此外还研究了炔的单取代碘化及铜粉促进1-碘炔的自身偶联反应合成1,3-共轭丁二炔。
论文共分为四章。
第一章：有机碱催化剂在有机合成中的应用
对有机碱为催化剂在有机合成中的应用做了详细的综述。
第二章：Bu3P和DMAP催化长链炔酮和磺酰亚胺的环化反应研究
本章系统研究了有机碱催化炔酮和磺酰亚胺的环加成反应合成氮杂环戊烷和氮杂环丁烷。当以甲苯为溶剂,Bu3P为催化剂催化炔酮和磺酰亚胺的反应可以得到较好产率的多官能团的氮杂环戊烷；以DMAP代替Bu3P为催化剂,二氯甲烷为溶剂得到中等至较好收率的全取代氮杂环丁烷。上述两个环加成反应所得的产物结构都具有很好的立体选择性。
第三章：有机碱催化基于丙炔酸酯的方法学研究
详细研究有机碱催化的丙炔酸酯与邻羟基p-二酮,邻羟基苯乙酮,芳香醛的各种反应：(1)邻羟基p-二酮在PPh3的催化下可以对丙炔酸酯进行α-加成,然后进一步通过C-C键断裂反应过程得到多官能团的丙烯酸酯化合物;(2)PPh3促进的邻羟基苯乙酮对丙炔酸酯的双α-加成反应合成功能化的1,4-戊二烯化合物;(3)丙炔酸酯和邻羟基苯乙酮先后在三级胺DABCO催化和KOBut的促进下得到苯并吡喃酮衍生物；(4)丙炔酸酯和芳香醛在PPh3的存在作用下通过多分子反应得到复杂官能团的丙烯酸酯化合物。
第四章：炔的单取代碘化及1-碘炔自身偶联反应
分别研究了在有机碱DMAP和无机碱K2CO3的作用下促进芳基乙炔和端基炔酮的直接单取代碘化反应,并利用铜粉可以促进1-碘炔的自身偶联反应得到1,3-共轭丁二炔。
随着对有机碱催化贫电子炔反应研究的不断深入,我们进一步拓宽了有机碱催化在有机合成中应用范围,为合成一些具有潜在应用价值的有机中间体提供了简单合成方法。
The dissertation is mainly focused on the application of organic base as catalyst to catalyzed reactions based on the electronic-deficient alkynes. Except that, direct iodination of monosubstituted acetylernes was also studied and the iodoacetylenes were used to synthesis of 1,3-butadiynes in the presence of copper powder.
This dissertation includes four chapters.
Chapter one:application of organic base as catalyst in organic synthesis.
In this chapter, detailed review was systematically described about the application of organic base as catalyst in organic synthesis.
Chapter two:cycloaddition of alkynyl ketones with N-Tosylimines catalyzed by Bu3P and DMAP.
Cycloadditon of alkynyl ketones with N-Tosylimines catalyzed by organic base to synthesize azetidines and pyrrolidines were systematically described. In the reaction of alkynyl ketones with N-Tosylimines catalyzed by Bu3P in toluene, highly functionalized pyrrolidines were formed in good to excellent yields. When DMAP was in place of Bu3P as catalyst to facilitate the cycloaddition, a completely substituted azetidines were produced in moderate to good yields in CH2CI2. Both of cyclization reactions proceeded smoothly with complete stereoslectivity.
Chapter three:the study of organic base catalyzed reactions based on the terminal alkynoates.
The reactions of terminal alkynoates with 1-(o-hydroxyaryl)-1,3-diketones, 2-hydroacetophenone, aromatic aldehydes catalyzed by organic base were detailed researched, respectively. (1) PPh3-catalyzed a-addition of 1-(o-hydroxyaryl)-1,3-diketones to terminal alkynoates involving carbon-carbon bond cleavage to give multifunctional vinylesters is described; (2) PPh3-mediated double a-addition reaction of ortho-acylphenols to ethyl propiolates to generate functionalized 1,4-pentadienes; (3) the reaction of 2-hydroacetophenone and terminal alkynoate successively catalyzed by DABCO and mediated by KOBut to synthesis of chromanone derivative. (4) PPh3-catalyzed multicomponent reaction of terminal alkynoates with aromatic aldehydes to afford multifunctional vinylesters.
Chapter four:iodination of monosubstituted acetylenes and homocoupling of 1-iodoalkynes.
Reaction of aryl acetylenes with molecular iodine in the presence of DMAP gave the iodoacetylenes, meanwhile, iodination of aryl acetylenic ketones using K2CO3 as base was also described. Furthermore, homocoupling of iodoacetylenes in the presence of copper powder gave the symmetrical 1,3-butadiynes was investigated.
With the development of study of organic base catalyzed reaction based on the electronic-deficient alkyne, we have extended the scope of application of organic base as catalyst in organic synthesis. Moreover, we have provided some straightforward methods to synthesis of potential organic intermediates.
论文共分为四章。
第一章：有机碱催化剂在有机合成中的应用
对有机碱为催化剂在有机合成中的应用做了详细的综述。
第二章：Bu3P和DMAP催化长链炔酮和磺酰亚胺的环化反应研究
本章系统研究了有机碱催化炔酮和磺酰亚胺的环加成反应合成氮杂环戊烷和氮杂环丁烷。当以甲苯为溶剂,Bu3P为催化剂催化炔酮和磺酰亚胺的反应可以得到较好产率的多官能团的氮杂环戊烷；以DMAP代替Bu3P为催化剂,二氯甲烷为溶剂得到中等至较好收率的全取代氮杂环丁烷。上述两个环加成反应所得的产物结构都具有很好的立体选择性。
第三章：有机碱催化基于丙炔酸酯的方法学研究
详细研究有机碱催化的丙炔酸酯与邻羟基p-二酮,邻羟基苯乙酮,芳香醛的各种反应：(1)邻羟基p-二酮在PPh3的催化下可以对丙炔酸酯进行α-加成,然后进一步通过C-C键断裂反应过程得到多官能团的丙烯酸酯化合物;(2)PPh3促进的邻羟基苯乙酮对丙炔酸酯的双α-加成反应合成功能化的1,4-戊二烯化合物;(3)丙炔酸酯和邻羟基苯乙酮先后在三级胺DABCO催化和KOBut的促进下得到苯并吡喃酮衍生物；(4)丙炔酸酯和芳香醛在PPh3的存在作用下通过多分子反应得到复杂官能团的丙烯酸酯化合物。
第四章：炔的单取代碘化及1-碘炔自身偶联反应
分别研究了在有机碱DMAP和无机碱K2CO3的作用下促进芳基乙炔和端基炔酮的直接单取代碘化反应,并利用铜粉可以促进1-碘炔的自身偶联反应得到1,3-共轭丁二炔。
随着对有机碱催化贫电子炔反应研究的不断深入,我们进一步拓宽了有机碱催化在有机合成中应用范围,为合成一些具有潜在应用价值的有机中间体提供了简单合成方法。
The dissertation is mainly focused on the application of organic base as catalyst to catalyzed reactions based on the electronic-deficient alkynes. Except that, direct iodination of monosubstituted acetylernes was also studied and the iodoacetylenes were used to synthesis of 1,3-butadiynes in the presence of copper powder.
This dissertation includes four chapters.
Chapter one:application of organic base as catalyst in organic synthesis.
In this chapter, detailed review was systematically described about the application of organic base as catalyst in organic synthesis.
Chapter two:cycloaddition of alkynyl ketones with N-Tosylimines catalyzed by Bu3P and DMAP.
Cycloadditon of alkynyl ketones with N-Tosylimines catalyzed by organic base to synthesize azetidines and pyrrolidines were systematically described. In the reaction of alkynyl ketones with N-Tosylimines catalyzed by Bu3P in toluene, highly functionalized pyrrolidines were formed in good to excellent yields. When DMAP was in place of Bu3P as catalyst to facilitate the cycloaddition, a completely substituted azetidines were produced in moderate to good yields in CH2CI2. Both of cyclization reactions proceeded smoothly with complete stereoslectivity.
Chapter three:the study of organic base catalyzed reactions based on the terminal alkynoates.
The reactions of terminal alkynoates with 1-(o-hydroxyaryl)-1,3-diketones, 2-hydroacetophenone, aromatic aldehydes catalyzed by organic base were detailed researched, respectively. (1) PPh3-catalyzed a-addition of 1-(o-hydroxyaryl)-1,3-diketones to terminal alkynoates involving carbon-carbon bond cleavage to give multifunctional vinylesters is described; (2) PPh3-mediated double a-addition reaction of ortho-acylphenols to ethyl propiolates to generate functionalized 1,4-pentadienes; (3) the reaction of 2-hydroacetophenone and terminal alkynoate successively catalyzed by DABCO and mediated by KOBut to synthesis of chromanone derivative. (4) PPh3-catalyzed multicomponent reaction of terminal alkynoates with aromatic aldehydes to afford multifunctional vinylesters.
Chapter four:iodination of monosubstituted acetylenes and homocoupling of 1-iodoalkynes.
Reaction of aryl acetylenes with molecular iodine in the presence of DMAP gave the iodoacetylenes, meanwhile, iodination of aryl acetylenic ketones using K2CO3 as base was also described. Furthermore, homocoupling of iodoacetylenes in the presence of copper powder gave the symmetrical 1,3-butadiynes was investigated.
With the development of study of organic base catalyzed reaction based on the electronic-deficient alkyne, we have extended the scope of application of organic base as catalyst in organic synthesis. Moreover, we have provided some straightforward methods to synthesis of potential organic intermediates.
引文
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10. The crystal data of 3b has been deposited in CCDC with number 682411. Empirical Formula: C416H384Br16N16O48S16; Formula Weight:8166.91; Crystal color, Habit:colorless, prismatic; Crystal Dimensions:0.24 x 0.22 x0.16 mm; Crystal System:monoclinic; Lattice Type: primitive; Lattice Parameters:a= 39.435(5) A, b= 15.399(2) A, c= 15.384(2) A, α= 90°,β= 99.734(3)°, γ= 90°, V= 9208(2) A3; Space group:P 121/c 1; Z= 1; Dcalc= 1.473 g/cm3; F000 = 4192; Diffractometer:Rigaku AFC7R; Residuals:R; Rw:0.0663,0.1228.
11. The crystal data of 5s has been deposited in CCDC with number 688638. Empirical Formula: C26H23BrN2O5S; Formula Weight:555.43; Crystal color, Habit:colorless, prismatic; Crystal Dimensions:0.26 × 0.18×0.04 mm; Crystal System:monoclinic; Lattice Type:primitive; Lattice Parameters:a=13.117(5) A, b=18.601(5) A, c=11.063 (5) A, α=90.000(5)°, β= 106.678(5)°, γ= 90.000(5)°, V= 2585.7(17) A3; Space group:P 21/c; Z= 4; Dcalc= 1.427 g/cm3; F000=1136; Diffractometer:Gemini s ultra oxford diffraction; Residuals:R; Rw: 0.0447,0.1147.
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9. The crystal data of 17a has been deposited in CCDC with number 711329. Empirical Formula: C20H18O5; Formula Weight:338.34; Crystal color. Habit:colorless, prismatic; Crystal Dimensions:0.42×0.40×0.34 mm; Crystal System:monoclinic; Lattice Type:primitive; Lattice Parameters:a=11.165(5)A, b=6.291(5)A, c=13.510 (5) A, α= 90.000(5)°,β= 114.011(5)°, γ=90.000(5)°, V= 866.8(9) A3; Space group:P 21; Z=2;Dcalc=1.296 g/cm3; Fooo= 356; Diffractometer:Gemini s ultra oxford diffraction; Residuals:R; Rw:0.0222, 0.0597.
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27.X-ray data of 43f has been deposited in CCDC as deposition number CCDC 674219. Empirical Formula:C24H22N2010；Formula Weight:498.44；Crystal color,Habit:colorless, prismatic:Crystal Dimensions:0.10×0.04×0.02mm；Crystal System:monoclinic；Lattice Type:primitive；Lattice Parameters:a=12.513(3)A,b=8.2665(17)A,c=23.483(5)A,α= 90°,β=105.11(3)°,γ=90°,V=2345.0(8)A3；Space group:P2(1)/n；Zvalue=4；Dcalc= 1.412 g/cm3；F000=1040；Diffractometer:Rigaku AFC7R；Residuals:R；Rw:0.0499,0.1203.
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10. The crystal data of 3b has been deposited in CCDC with number 682411. Empirical Formula: C416H384Br16N16O48S16; Formula Weight:8166.91; Crystal color, Habit:colorless, prismatic; Crystal Dimensions:0.24 x 0.22 x0.16 mm; Crystal System:monoclinic; Lattice Type: primitive; Lattice Parameters:a= 39.435(5) A, b= 15.399(2) A, c= 15.384(2) A, α= 90°,β= 99.734(3)°, γ= 90°, V= 9208(2) A3; Space group:P 121/c 1; Z= 1; Dcalc= 1.473 g/cm3; F000 = 4192; Diffractometer:Rigaku AFC7R; Residuals:R; Rw:0.0663,0.1228.
11. The crystal data of 5s has been deposited in CCDC with number 688638. Empirical Formula: C26H23BrN2O5S; Formula Weight:555.43; Crystal color, Habit:colorless, prismatic; Crystal Dimensions:0.26 × 0.18×0.04 mm; Crystal System:monoclinic; Lattice Type:primitive; Lattice Parameters:a=13.117(5) A, b=18.601(5) A, c=11.063 (5) A, α=90.000(5)°, β= 106.678(5)°, γ= 90.000(5)°, V= 2585.7(17) A3; Space group:P 21/c; Z= 4; Dcalc= 1.427 g/cm3; F000=1136; Diffractometer:Gemini s ultra oxford diffraction; Residuals:R; Rw: 0.0447,0.1147.
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27.X-ray data of 43f has been deposited in CCDC as deposition number CCDC 674219. Empirical Formula:C24H22N2010；Formula Weight:498.44；Crystal color,Habit:colorless, prismatic:Crystal Dimensions:0.10×0.04×0.02mm；Crystal System:monoclinic；Lattice Type:primitive；Lattice Parameters:a=12.513(3)A,b=8.2665(17)A,c=23.483(5)A,α= 90°,β=105.11(3)°,γ=90°,V=2345.0(8)A3；Space group:P2(1)/n；Zvalue=4；Dcalc= 1.412 g/cm3；F000=1040；Diffractometer:Rigaku AFC7R；Residuals:R；Rw:0.0499,0.1203.
28.Newcomb,M.；Miranda,N.；Huang,X.；C rich,D.J.Am.Chem.Soc.2000,122,6128.
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