CN111072555B - 制备杂环砜类有机化合物的方法 - Google Patents
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Abstract
本发明公开了杂环芳基卤素与芳基亚磺酸盐制备杂环砜类有机化合物的方法,该方法包括如下步骤:在惰性气体保护下,按照杂环芳基卤素类化合物:苯亚磺酸盐类化合物:无机碱:HEH之间的摩尔比为1:2:1.5:0.2,将上述反应物加入到配备搅拌装置的反应容器中,再加入二甲亚砜,于蓝色LED照射,室温下搅拌反应24小时,得到杂环砜类有机化合物。本发明首次在不添加任何辅助过渡金属催化剂和贵金属光敏剂的情况下,以HEH作为催化剂,实现了一系列杂环芳基卤素与苯亚磺酸盐的交叉偶联反应。另外,本发明整个过程绿色、高效且易于操作,是一种合成杂环砜类有机化合物的好方法。
Description
技术领域
本发明属于催化化学技术领域,具体涉及2,6-二甲基-1,4-二氢-3,5-吡啶二羧酸二乙酯 (HEH)作为可见光还原催化剂诱导无过渡金属催化杂环芳基卤素与芳基亚磺酸盐制备杂环砜类有机化合物的方法。
背景技术
有机砜类化合物不仅是一类重要的有机配合物,而且广泛存在于天然产物、生物活性物质和药物分子中。为了合成这类化合物,已经开发了多种方法。比如说,在较高的温度下,通过钯或铜催化杂环芳基卤素和亚磺酸盐的交叉偶联反应;或者通过过量的无机氧化剂氧化硫醚得到该类化合物,但该方法选择性差,易产生亚砜等副产物,也产生大量的废弃物。少些课题组通过钌或铱贵金属配合物作为光敏剂,再与镍催化剂结合,实现了杂环芳基卤素与亚磺酸盐的交叉偶联反应。但是,这些方法需要昂贵的Ir/Ru有机金属配合物和过渡金属催化剂的结合,这不仅增加了成本,而且涉及毒性的风险;另外高能紫外光与官能团不相容,会引起副作用。
发明内容
为了克服上述技术问题,本发明提供了一种全新的2,6-二甲基-1,4-二氢-3,5-吡啶二羧酸二乙酯 (HEH)催化体系,实现了砜类化合物的合成。即在不添加任何辅助过渡金属催化剂的情况下,以HEH作为催化剂,以碳酸铯作为碱,在蓝色LED(10 W, 波长为460-485nm)照射下,实现了一系列杂环芳基卤素与苯基亚磺酸盐的交叉偶联反应,克服了现有技术认为芳基化试剂与亚磺酸盐的芳基化反应,因芳基卤素具有较高的还原电势而不能通过可见光诱导的问题。此外,本发明可以较高收率获得砜类化合物。本发明的整个催化过程绿色、高效且易于操作,是一种合成杂环砜类有机化合物的好方法。
具体而言,本发明采用如下技术方案:
一种制备杂环砜类有机化合物的方法,以2,6-二甲基-1,4-二氢-3,5-吡啶二羧酸二乙酯为催化剂,杂环芳基卤素与苯基亚磺酸盐为原料反应制备杂环砜类化合物。
2,6-二甲基-1,4-二氢-3,5-吡啶二羧酸二乙酯在催化杂环芳基卤素与苯基亚磺酸盐反应制备杂环砜类化合物的应用。
本发明中,所述反应为在室温下,蓝色LED (10 W, 波长为460-485 nm)照射下反应24小时。
本发明中,所述反应在惰性气体保护下、碱存在下、溶剂中进行;所述2,6-二甲基-1,4-二氢-3,5-吡啶二羧酸二乙酯的用量为杂环芳基卤素摩尔量的20%;优选的,杂环芳基卤素、苯基亚磺酸盐、碱的摩尔比为1:2:1.5。
本发明的反应在无过渡金属光敏剂和过渡金属催化剂存在下进行,有效解决了现有技术需要辅助(过渡)金属催化剂的问题。
本发明中,所述杂环芳基卤素具有如下结构式中的一种:
本发明公开的HEH作为可见光还原催化剂诱导无过渡金属催化杂环芳基卤素与苯基亚磺酸盐制备杂环砜类化合物的应用,包括如下步骤:在惰性气体保护下,按照杂环芳基卤素: 苯基亚磺酸盐:无机碱:HEH=1:2:1.5:0.2的摩尔比,将上述反应物加入到配备搅拌装置的反应容器中,再加入二甲亚砜,于蓝色LED (10 W, 波长为460-485 nm)照射下,室温搅拌反应24小时,得到砜类化合物。
本发明中,惰性气体选自氮气、氦气、氖气、氩气中的任意一种,优选氮气;所述碱为无机碱中的任意一种,所述无机碱选自碳酸铯、碳酸钠、碳酸钾、磷酸钾、磷酸氢二钾、醋酸钠中的任意一种,优选碳酸铯;所述苯基亚磺酸盐为苯亚磺酸钠。
本发明中,所述催化剂HEH具有如式(I)所示的结构式:
本发明中,第一原料杂环芳基卤素中的卤素位点与第二原料亚磺酸盐的亚磺酸位点反应制备杂环砜类化合物,反应明确。
优选的,在上述杂环砜类化合物的合成方法中,所述搅拌装置为磁力搅拌装置。
优选的,在上述杂环砜类化合物的合成方法中,所述反应容器为密封反应管。
优选的,在上述杂环砜类化合物的合成方法中,所述反应是在蓝色LED (10 W, 波长为460-485 nm),室温下进行。
优选的,在上述杂环砜类化合物的合成方法中,所述反应的时间为24小时。
与现有技术相比,采用上述技术方案的本发明具有下列优点:本发明首次在不添加任何辅助过渡金属催化剂的情况下,以HEH作为催化剂,以碳酸铯作为碱,在蓝色LED (10W, 波长为460-485 nm)照射下,实现了一系列杂环芳基卤素与苯基亚磺酸盐的交叉偶联反应。此外,本发明可以较高收率获得杂环砜类化合物。整个过程绿色、高效且易于操作,是一种合成杂环砜类化合物的好方法。
具体实施方式
下面将结合具体的实施例对本发明做出进一步的描述。除非另有说明,下列实施例中所使用的试剂、材料、仪器等均可通过商业手段获得。本发明的反应在无金属催化剂或者过渡金属催化剂存在下进行,仅采用杂环芳基卤素、苯基亚磺酸盐、无机碱与HEH、DMSO为原料;本发明实施例的反应在室温下进行,蓝色LED 波长为460-485 nm(10 W)。
实施例1:HEH催化体系催化4-碘吡啶和苯亚磺酸钠反应。
将4-碘吡啶(0.2 mmol),苯亚磺酸钠(0.4 mmol),Cs2CO3(0.3 mmol),HEH(20mol%,0.04 mmol)以及DMSO(1 mL)加入带有磁力搅拌子的干燥的反应管中,接着该反应管用N2置换3次,在蓝色LED照射下,搅拌反应24 h。反应结束后,加入5 mL水,然后用3×5 mL乙酸乙酯萃取,合并有机相,有机相再用无水硫酸钠干燥,过滤,滤液旋转蒸发浓缩后,经硅胶色谱柱层析分离,得到目标产物(收率68%)。将更换为K2CO3,其余不变,得到目标产物(收率62%)。
1H-NMR (400 MHz, CDCl3, ppm): δ 8.80 (s, 2H), 7.95 (d, J = 7.1 Hz,2H), 7.75 (d, J = 1.7 Hz, 2H), 7.61 (d, J = 6.7 Hz, 1H), 7.54 (d, J = 7.0 Hz,2H)。
13C-NMR (101 MHz, CDCl3, ppm): δ 151.3, 149.9, 139.8, 134.3, 129.8,128.2, 120.7。
实施例2:HEH催化体系催化4-溴-2-三氟甲基吡啶和苯亚磺酸钠反应。
将4-溴-2-三氟甲基吡啶(0.2 mmol),苯亚磺酸钠(0.4 mmol),Cs2CO3(0.3 mmol),HEH(20 mol%)以及DMSO(1 mL)加入带有磁力搅拌子的干燥的反应管中,接着该反应管用N2置换3次,在蓝色LED照射下,搅拌反应24 h。反应结束后,加入5 mL水,然后用3×5 mL乙酸乙酯萃取,合并有机相,有机相再用无水硫酸钠干燥,过滤,滤液旋转蒸发浓缩后,经硅胶色谱柱层析分离,得到目标产物(收率85%)。
1H NMR (400 MHz, CDCl3, ppm): δ = 8.94 (d, J = 4.9 Hz, 1H), 8.13 (s,1H), 7.98 (t, J = 7.3 Hz, 3H), 7.69 (t, J = 7.4 Hz, 1H), 7.60 (t, J = 7.6 Hz,2H)。
13C NMR (101 MHz, CDCl3, ppm): δ = 152.2, 151.8, 150.2 (q, J = 36.4Hz), 139.1, 134.9, 130.2, 128.6, 123.8, 120.9 (q, J = 277.8 Hz), 118.0 (q, J= 2.0 Hz)。
实施例3:HEH催化体系催化2-溴-6-三氟甲基吡啶和苯亚磺酸钠反应。
将2-溴-6-三氟甲基吡啶(0.2 mmol),苯亚磺酸钠(0.4 mmol),Cs2CO3(0.3 mmol),HEH(20 mol%)以及DMSO(1 mL)加入带有磁力搅拌子的干燥的反应管中,接着该反应管用N2置换3次,在蓝色LED照射下,搅拌反应24 h。反应结束后,加入5 mL水,然后用3×5 mL乙酸乙酯萃取,合并有机相,有机相再用无水硫酸钠干燥,过滤,滤液旋转蒸发浓缩后,经硅胶色谱柱层析分离,得到目标产物(收率81%)。
1H NMR (400 MHz, CDCl3, ppm): δ = 8.38 (d, J = 7.9 Hz, 1H), 8.12 (dd,J = 14.1, 7.6 Hz, 3H), 7.82 (d, J = 7.8 Hz, 1H), 7.65 (t, J = 7.3 Hz, 1H),7.56 (t, J = 7.6 Hz, 2H)。
13C NMR (101 MHz, CDCl3, ppm): δ = 159.6, 149.3 (q, J = 36.4 Hz),140.2, 138.1, 134.5, 129.6, 129.4, 124.5, 123.7 (q, J = 2.0 Hz), 120.7 (q, J= 274.8 Hz)。
实施例4:HEH催化体系催化2-溴-6-氰基吡啶和苯亚磺酸钠反应。
将2-溴-6-氰基吡啶(0.2 mmol),苯亚磺酸钠(0.4 mmol),Cs2CO3(0.3 mmol),HEH(20 mol%)以及DMSO(1 mL)加入带有磁力搅拌子的干燥的反应管中,接着该反应管用N2置换3次,在蓝色LED照射下,搅拌反应24 h。反应结束后,加入5 mL水,然后用3×5 mL乙酸乙酯萃取,合并有机相,有机相再用无水硫酸钠干燥,过滤,滤液旋转蒸发浓缩后,经硅胶色谱柱层析分离,得到目标产物(收率78%)。
1H NMR (400 MHz, CDCl3, ppm): δ = 8.41 (d, J = 7.9 Hz, 1H), 8.10 (dd,J = 20.2, 7.8 Hz, 3H), 7.83 (d, J = 7.7 Hz, 1H), 7.68 (t, J = 7.2 Hz, 1H),7.58 (t, J = 7.5 Hz, 2H)。
13C NMR (101 MHz, CDCl3, ppm): δ = 160.7, 139.9, 137.7, 134.7, 134.5,131.3, 129.6, 125.0, 115.9。
实施例5:HEH催化体系催化2-溴喹啉和苯亚磺酸钠反应。
将2-溴喹啉(0.2 mmol),苯亚磺酸钠(0.4 mmol),Cs2CO3(0.3 mmol),HEH(20mol%)以及DMSO(1 mL)加入带有磁力搅拌子的干燥的反应管中,接着该反应管用N2置换3次,在蓝色LED照射下,搅拌反应24 h。反应结束后,加入5 mL水,然后用3×5 mL乙酸乙酯萃取,合并有机相,有机相再用无水硫酸钠干燥,过滤,滤液旋转蒸发浓缩后,经硅胶色谱柱层析分离,得到目标产物(收率72%)。
1H NMR (400 MHz, CDCl3, ppm): δ = 8.39 (d, J = 8.5 Hz, 1H), 8.30–8.04(m, 4H), 7.88 (d, J = 8.1 Hz, 1H), 7.79 (t, J = 7.5 Hz, 1H), 7.67 (t, J = 7.4Hz, 1H), 7.61 (t, J = 7.3 Hz, 1H), 7.54 (t, J = 7.5 Hz, 2H)。
13C NMR (101 MHz, CDCl3, ppm): δ = 158.3, 147.7, 139.4, 139.0, 133.9,131.2, 130.7, 129.4, 129.3, 129.3, 129.1, 127.9, 118.0。
实施例6:HEH催化体系催化2-碘噻吩和苯亚磺酸钠反应。
将2-碘噻吩(0.2 mmol),苯亚磺酸钠(0.4 mmol),Cs2CO3(0.3 mmol),HEH(20mol%)以及DMSO(1 mL)加入带有磁力搅拌子的干燥的反应管中,接着该反应管用N2置换3次,在蓝色LED照射下,搅拌反应24 h。反应结束后,加入5 mL水,然后用3×5 mL乙酸乙酯萃取,合并有机相,有机相再用无水硫酸钠干燥,过滤,滤液旋转蒸发浓缩后,经硅胶色谱柱层析分离,得到目标产物(收率51%)。
1H NMR (400 MHz, CDCl3, ppm): δ = 7.99 (d, J = 7.6 Hz, 2H), 7.70 (s,1H), 7.64 (d, J = 4.5 Hz, 1H), 7.61–7.56 (m, 1H), 7.52 (t, J = 7.3 Hz, 2H),7.08 (s, 1H)。
13C NMR (101 MHz, CDCl3, ppm): δ = 143.3, 142.3, 134.1, 133.6, 133.5,129.5, 128.1, 127.6。
实施例7:HEH催化体系催化8-氯-3-碘喹啉和苯亚磺酸钠反应。
将8-氯-3-碘喹啉(0.2 mmol),苯亚磺酸钠(0.4 mmol),Cs2CO3(0.3 mmol),HEH(20mol%)以及DMSO(1 mL)加入带有磁力搅拌子的干燥的反应管中,接着该反应管用N2置换3次,在蓝色LED照射下,搅拌反应24 h。反应结束后,加入5 mL水,然后用3×5 mL乙酸乙酯萃取,合并有机相,有机相再用无水硫酸钠干燥,过滤,滤液旋转蒸发浓缩后,经硅胶色谱柱层析分离,得到目标产物(收率83%)。
1H NMR (400 MHz, CDCl3, ppm): δ 9.36 (d, J = 2.2 Hz, 1H), 8.84 (d, J =2.2 Hz, 1H), 8.06–8.01 (m, 2H), 7.98 (dd, J = 7.5, 1.2 Hz, 1H), 7.90 (dd, J =8.2, 1.1 Hz, 1H), 7.64–7.58 (m, 2H), 7.57–7.51 (m, 2H)。
13C NMR (101 MHz, CDCl3, ppm): δ = 148.0, 145.7, 140.9, 137.4, 136.1,134.4, 134.2, 132.9, 129.9, 128.6, 128.4, 128.1, 128.1。
实施例8:HEH催化体系催化2-溴喹啉和苯亚磺酸钠反应。
将2-溴喹啉(0.2 mmol),苯亚磺酸钠(0.4 mmol),Cs2CO3(0.3 mmol),HEH(20mol%)以及DMSO(1 mL)加入带有磁力搅拌子的干燥的反应管中,接着该反应管用N2置换3次,在蓝色LED照射下,搅拌反应24 h。反应结束后,加入5 mL水,然后用3×5 mL乙酸乙酯萃取,合并有机相,有机相再用无水硫酸钠干燥,过滤,滤液旋转蒸发浓缩后,经硅胶色谱柱层析分离,得到目标产物(收率72%)。
1H-NMR (400 MHz, CDCl3, ppm): δ 8.39 (d, J = 8.5 Hz, 1H), 8.30 – 8.04(m, 4H), 7.88 (d, J = 8.1 Hz, 1H), 7.79 (t, J = 7.5 Hz, 1H), 7.67 (t, J = 7.4Hz, 1H), 7.61 (t, J = 7.3 Hz, 1H), 7.54 (t, J = 7.5 Hz, 2H)。
13C-NMR (101 MHz, CDCl3, ppm): δ 158.3, 147.7, 139.4, 139.0, 133.9,131.2, 130.7, 129.4, 129.3, 129.3, 129.1, 127.9, 118.0。
Claims (9)
2.根据权利要求1所述制备杂环砜类有机化合物的方法,其特征在于:所述反应在惰性气体保护下进行。
3.根据权利要求1所述制备杂环砜类有机化合物的方法,其特征在于:所述2,6-二甲基-1,4-二氢-3,5-吡啶二羧酸二乙酯的用量为杂环芳基卤素摩尔量的20%。
4.根据权利要求3所述制备杂环砜类有机化合物的方法,其特征在于:所述杂环芳基卤素、苯基亚磺酸盐、碱的摩尔比为1:2:1.5。
6.根据权利要求5所述的应用,其特征在于,所述反应为在室温下进行。
7.根据权利要求5所述的应用,其特征在于:所述反应在惰性气体保护下进行。
8.根据权利要求5所述的应用,其特征在于:杂环芳基卤素、苯基亚磺酸钠、碱的摩尔比为1:2:1.5。
9.根据权利要求5所述的应用,其特征在于:所述2,6-二甲基-1,4-二氢-3,5-吡啶二羧酸二乙酯的用量为杂环芳基卤素摩尔量的20%。
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