CN113731506A - 杯[4]芳烃酰胺化合物协助钯催化脂肪醛c-h芳基化反应的方法 - Google Patents
杯[4]芳烃酰胺化合物协助钯催化脂肪醛c-h芳基化反应的方法 Download PDFInfo
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Abstract
本发明属于有机合成领域。具体公开了一种杯[4]芳烃酰胺化合物协助过渡金属钯催化脂肪醛C‑H键芳基化反应的方法。反应的步骤为,在30mL的反应管中加入脂肪醛、芳基碘化物、杯芳烃配体、银盐添加剂、金属钯催化剂、六氟异丙醇和醋酸混合溶剂。100℃氮气保护下剧烈搅拌24h。反应结束后,硅藻土助滤除去不溶物,浓缩反应液,通过快速柱色谱法即可获得纯的目标产物。该方法直接对脂肪醛C‑H进行芳基化合反应,无需对底物进行预制备,具有潜在的应用价值。
Description
技术领域
本发明属于有机合成领域,具体涉及一种杯[4]芳烃酰胺化合物协助钯催化脂肪醛C-H芳基化反应的方法。
背景技术
脂肪醛是天然产物和药物中最为常见的结构单元之一,而且还是有机合成中的关键中间体,因此脂肪醛的衍生化已经引起有机化学家的广泛关注。在醛基的ipso和α位置进行官能化的方法已有很好的方法报道,脂肪醛的β-官能化主要依赖于向α,β不饱和醛中添加亲核试剂,利用这种方法通常需要对饱和前体进行预官能化,而脂肪醛的直接β官能化的报道却很少见。
发明内容
本发明的目的是:提供一种杯芳烃酰胺化合物协助钯催化脂肪醛C-H键芳基化反应的方法,包括以下步骤:
(1)以脂肪醛和芳基碘化物为原料,过渡金属钯作为催化剂,银盐作为添加剂,杯[4]芳烃酰胺化合物作为配体,六氟异丙醇和醋酸作为混合溶剂,氮气保护条件下进行反应;
其中,脂肪醛为三甲基乙醛、甲基乙基丙基醛、甲基乙基丁基醛;芳基碘化物为4-碘苯甲酸甲酯、3-碘苯甲酸甲酯、4-碘苯甲酸乙酯、4-硝基碘苯、4-甲氧基碘苯;
脂肪醛优选为三甲基乙醛;芳基碘化物优选为4-碘苯甲酸甲酯;
脂肪醛和芳基碘化物的摩尔比为1:2。
杯[4]芳烃酰胺化合物的添加量为40mol%-100mol%;优选为80mol%;
过渡金属钯催化剂为醋酸钯、三氟乙酸钯、氯化钯、溴化钯;其添加量为10mol%-20mol%;
过渡金属钯催化剂优选为醋酸钯;其添加量优选为20mol%。
银盐为三氟乙酸银、氧化银、碳酸银、乙酸银、三氟磺酸银;添加量为1.5-2.5当量。
银盐优选为三氟乙酸银;其添加量优选为2.0当量。
六氟异丙醇和醋酸的体积比为1:1。
反应温度为100℃,反应时间为12-48h,优选为24h。
(2)步骤(1)反应结束后,硅藻土过滤除去不溶物,浓缩后经石油醚和乙酸乙酯柱层析分离,纯化得芳基化产物。
有益效果:该方法能够快速、有效地一步制备脂肪族三级醛β位的芳基衍生物,大大提高这些含醛基衍生物的价值。此外,该反应方法在对药物和生物活性分子等复杂有机分子的直接精准修饰具有一定的应用前景。
具体实施方式
下面结合具体实施例,进一步对本发明进行阐述,应理解,引用实施例仅用于说明本发明,而不用于限制本发明的内容。
实施例中采用薄层色谱法(GF254硅胶板)监测反应进程,柱色谱法(200~300目硅胶柱,洗脱剂为石油醚和乙酸乙酯的混合液)纯化粗产物。实施例中给出的产率为经色谱柱纯化后的产物收率。
实施例1
本实施例为杯[4]芳烃酰胺化合物配体L1的合成方法,具体步骤如下:
以杯[4]芳烃羧酸化合物1(合成方法见:Tetrahedron,2017,73(1),78-85)和胺类化合物2(合成方法见:Journal of Medicinal Chemistry,2009,52(16),5093-5107)作为起始原料,经过常规的缩合反应和钯碳还原反应(合成方法见:合成化学,2017,25(3),207-212.)制得配体L1(白色固体),两步总收率为37%.1H NMR(300MHz,DMSO)δ8.78–8.38(m,2H),7.71(br,1H),7.60(s,1H),7.15–6.71(m,3H),6.41–6.11(m,5H),4.40–4.28(m,4H),4.01–3.66(m,13H),3.28–3.15(m,4H),1.93–1.82(m,8H),1.10–0.86(m,12H).MS(ESI)calculated for C44H55N2O7[M+H]+:723,found:723.
实施例2
本实施例以三甲基乙醛和4-碘苯甲酸甲酯为底物,L1协助钯催化脂肪醛C-H键芳基化反应的主要影响因素如杯芳烃配体的添加量、过渡金属钯催化剂的种类、银盐的种类进行了系统的研究。
表1配体添加量对反应结果的影响
a试剂和条件:三甲基乙醛(0.2mmol),4-碘苯甲酸甲酯(0.4mmol),AgTFA(0.3mmol),Pd(OAc)2(0.04mmol),HFIP:HOAc=1:1(V:V,0.1M),N2,100℃,24h.
表2钯催化剂的种类对反应结果的影响
a试剂和条件:三甲基乙醛(0.2mmol),4-碘苯甲酸甲酯(0.4mmol),AgTFA(0.3mmol),L1(0.16mmol),HFIP:HOAc=1:1(V:V,0.1M),N2,100℃,24h.
表3银盐种类对反应结果的影响
a试剂和条件:三甲基乙醛(0.2mmol),4-碘苯甲酸甲酯(0.4mmol),Pd(OAc)2(0.04mmol),L1(0.16mmol),HFIP:HOAc=1:1(V:V,0.1M),N2,100℃,24h.
反应条件优化如表1、2、3所示,可得最佳的反应条件为:杯芳烃配体L1的添加量为80%,醋酸钯为过渡金属催化剂,三氟乙酸银为银盐添加剂。
实施例3
本实施例参照具体实施例2中最佳反应条件对杯芳烃L1协助的钯催化脂肪醛C-H键芳基化反应脂肪醛的底物适用范围进行了考察,实验方法为:在30mL的耐压管中加入脂肪醛(0.2mmol)、4-碘苯甲酸甲酯(0.4mmol,104.8mg)、三氟乙酸银(0.3mmol,66.3mg)、醋酸钯(0.04mmol,9.0mg)、六氟异丙醇和醋酸(1:1,0.1M)。100℃且氮气保护下剧烈搅拌24h。反应结束后冷却至室温,硅藻土助滤下除去不溶物,浓缩反应液,通过快速柱色谱法即可获得纯的目标产物。实验结果见表4。
表4杯芳烃协助的钯催化脂肪醛C-H键芳化反应脂肪醛的底物适用范围考察
实施例4
本实施例参照具体实施例2中最佳反应条件对杯芳烃L1协助的钯催化脂肪醛C-H键芳基化反应芳基碘苯的底物适用范围进行了考察,实验方法为:在30mL的反应管中加入三甲基乙醛(0.2mmol,17.2mg)、芳基碘苯(0.4mmol)、三氟乙酸银(0.3mmol,66.3mg)、醋酸钯(0.04mmol,9.0mg)、六氟异丙醇和醋酸(1:1,0.1M)。100℃且氮气保护下剧烈搅拌24h。反应结束后冷却至室温,硅藻土助滤下除去不溶物,浓缩反应液,通过快速柱色谱法即可获得纯的目标产物。实验结果见表5。
表5杯芳烃协助L1的钯催化脂肪醛C-H键芳化反应芳基碘苯的底物适用范围
根据反应结果分析和催化剂的结构构造,假设了可能的反应机理。
三甲基乙醛1与配体L1的缩合提供了亚胺中间体A。亚胺中间体A与金属钯配位,随后的环金属化反应通过位点选择性活化C-H生成相应的[5,5]-双环钯中间体B,此时,过渡金属催化剂的金属中心钯与杯芳烃空腔存在阳离子···π作用力有利于中间体B的生成,接下来,中间体B与芳基碘化物的氧化加成生成钯配合物C。最后,通过还原消除钯配合物C,然后进行配体解离和碘化物提取过程,生成了亚胺中间体D,该亚胺中间体D可以进一步转化为所需的产物3和配体L1。
可能的反应机理
对照例1
以三甲基乙醛和4-碘苯甲酸甲酯的反应为例,不加杯芳烃配体,反应不能进行,无法分离到目标产物。
以上述依据本发明的理想实施例为启示,通过上述的说明内容,相关工作人员完全可以在不偏离本项发明技术思想的范围内,进行多样的变更以及修改。本项发明的技术性范围并不局限于说明书上的内容,必须要根据权利要求范围来确定其技术性范围。
Claims (8)
1.一种杯[4]芳烃酰胺化合物协助过渡金属钯催化脂肪醛C-H键芳基化反应的方法,其特征在于:所述方法步骤如下:
(1)以脂肪醛和芳基碘化物为原料,过渡金属钯作为催化剂,银盐作为添加剂,杯[4]芳烃酰胺化合物作为配体,六氟异丙醇和醋酸作为混合溶剂,氮气保护条件下进行反应;
(2)步骤(1)反应结束后,硅藻土过滤除去不溶物,浓缩后经石油醚和乙酸乙酯柱层析分离,纯化得芳基化产物。
3.如权利要求1所述的杯[4]芳烃酰胺化合物协助过渡金属钯催化脂肪醛C-H键芳基化反应的方法,其特征在于:所述脂肪醛为三甲基乙醛、甲基乙基丙基醛、甲基乙基丁基醛;所述芳基碘化物为4-碘苯甲酸甲酯、4-碘苯甲酸乙酯、4-硝基碘苯、3-碘苯甲酸甲酯、4-甲氧基碘苯。
4.如权利要求3所述的杯[4]芳烃酰胺化合物协助过渡金属钯催化脂肪醛C-H键芳基化反应的方法,其特征在于:所述脂肪醛为三甲基乙醛;所述芳基碘化物为4-碘苯甲酸甲酯。
5.如权利要求1所述的杯[4]芳烃酰胺化合物协助过渡金属钯催化脂肪醛C-H键芳基化反应的方法,其特征在于:所述过渡金属钯催化剂为醋酸钯、三氟乙酸钯、氯化钯、溴化钯;银盐为三氟乙酸银、三氟磺酸银、碳酸银、氧化银、乙酸银。
6.如权利要求5所述的杯[4]芳烃酰胺化合物协助过渡金属钯催化脂肪醛C-H键芳基化反应的方法,其特征在于:所述过渡金属钯催化剂为醋酸钯,银盐为三氟乙酸银。
7.如权利要求1所述的杯[4]芳烃酰胺化合物协助过渡金属钯催化脂肪醛C-H键芳基化反应的方法,其特征在于:所述脂肪醛和芳基碘化物的摩尔比为1:2;所述杯[4]芳烃酰胺化合物的添加量为40mol%-100mol%;所述六氟异丙醇和醋酸的体积比为1:1。
8.如权利要求1所述的杯[4]芳烃酰胺化合物协助过渡金属钯催化脂肪醛C-H键芳基化反应的方法,其特征在于:催化剂添加量为10mol%-20mol%,银盐用量为1.5-2.5当量;反应温度为100℃,反应时间为12-48h。
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