脱硼氟烷基化反应研究进展
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摘要
氟烷基化反应作为有机氟化学领域的重要研究课题,能够直接将含氟基团引入有机分子,并通过含氟基团的"氟效应"改善有机分子的理化性质。以有机硼酸为代表的有机硼试剂具有对水及空气不敏感、反应活性高、官能团兼容性好、低毒等优点。近年来,诸多基于有机硼试剂的脱硼氟烷基化反应被报道。本文首先依据氟烷基化试剂在反应过程中体现的电子性质,从亲核型氟烷基化、亲电氟烷基化及自由基氟烷基化3个方面,对目前脱硼氟烷基化反应所涉及的氟试剂、催化剂、溶剂、气氛条件、反应收率、底物普适性及反应机理进行了归纳和总结;之后对近几年来新兴的光催化脱硼氟烷基化反应进行了单独介绍;最后从绿色化学角度对脱硼氟烷基化反应在光催化领域的发展趋势做了总结和展望。指出未来脱硼氟烷基化反应将沿着探索温和、高效、环境友好催化体系的趋势,发展更具环境、经济及社会效益的合成方法。
As a significant research topic in organic fluorine chemistry, fluoroalkylations could change the physicochemical properties of organic chemicals by directly introducing fluorinated groups to their molecules. In the past decades, many organic boron involved protodeboronized fluoroalkylations have been reported due to its advantages of air-and water-stable properties, high reactivity, outstanding functional group tolerance, and non-toxicity. According to the electron properties of fluoroalkyl reagents,a full survey of nucleophilic fluoroalkylations, electrophilic fluoroalkylations, and free radical fluoroalkylations has been reported in this review. And the related topics of fluoroalkyl reagents, catalysts,solvents, atmosphere conditions, reaction yields, substrates universality and reaction mechanisms have been discussed. Subsequently, the photoredox catalysis of protodeboronized fluoroalkylations rising in recent years were introduced separately. Finally, the development tendency of protodeboronized fluoroalkylations in photoredox catalysis was summarized and prospected from the viewpoint of green chemistry. In the future, protodeboronized fluoroalkylations will continue to explore mild, efficient and environmentally friendly catalytic systems, and to develop novel synthetic methods which are more environmentally, economically and socially beneficial.
As a significant research topic in organic fluorine chemistry, fluoroalkylations could change the physicochemical properties of organic chemicals by directly introducing fluorinated groups to their molecules. In the past decades, many organic boron involved protodeboronized fluoroalkylations have been reported due to its advantages of air-and water-stable properties, high reactivity, outstanding functional group tolerance, and non-toxicity. According to the electron properties of fluoroalkyl reagents,a full survey of nucleophilic fluoroalkylations, electrophilic fluoroalkylations, and free radical fluoroalkylations has been reported in this review. And the related topics of fluoroalkyl reagents, catalysts,solvents, atmosphere conditions, reaction yields, substrates universality and reaction mechanisms have been discussed. Subsequently, the photoredox catalysis of protodeboronized fluoroalkylations rising in recent years were introduced separately. Finally, the development tendency of protodeboronized fluoroalkylations in photoredox catalysis was summarized and prospected from the viewpoint of green chemistry. In the future, protodeboronized fluoroalkylations will continue to explore mild, efficient and environmentally friendly catalytic systems, and to develop novel synthetic methods which are more environmentally, economically and socially beneficial.
引文
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[9]潘菲,施章杰.过渡金属催化碳氢键三氟甲基化[J].化学学报,2012, 70(16):1679-1681.PAN Fei, SHI Zhangjie. Transition metal-catalyzed C—H trifluoromethylation[J]. Acta Chimica Sinica, 2012, 70(16):1679-1681.
[10] GILLIS E P, EASTMAN K J, HILL M D, et al. Applications of fluorine in medicinal chemistry[J]. Journal of Medicinal Chemistry, 2015, 58(21):8315-8359.
[11] ZHOU Y, WANG J, GU Z, et al. Next generation of fluorinecontaining pharmaceuticals, compounds currently in phaseⅡ-Ⅲclinical trials of major pharmaceutical companies:new structural trends and therapeutic areas[J]. Chemical Reviews, 2016, 116(2):422-518.
[12]王亚虎,韩民,张兰兰,等.芳基卤代物三氟甲基化反应的研究进展[J].化工新型材料, 2013, 41(4):169-171.WANG Yahu, HAN Min, ZHANG Lanlan, et al. Research progress on the trifluoromethylation reaction of aryl halides[J]. New Chemical Materials, 2013, 41(4):169-171.
[13]尹锋,李彦,王细胜.通过单电子氧化途径进行的钯催化碳—氢键三氟甲硫基化反应[J].中国科技论文, 2016, 11(18):2073-2076.YIN Feng, LI Yan, WANG Xisheng. Pd(II)-catalyzed trifluoromethylthiolation of C—H bonds via single electron oxidation[J]. China Science Paper, 2016, 11(18):2073-2076.
[14]张盼盼,吕龙,沈其龙.直接三氟甲硫基化试剂及方法的研究进展[J].化学学报, 2017, 75(8):744-769.ZHANG Panpan, LüLong, SHEN Qilong. Recent progress on direct trifluoromethylthiolating reagents and methods[J]. Acta Chimica Sinica, 2017, 75(8):744-769.
[15] HAGMANN W K. The many roles for fluorine in medicinal chemistry[J]. Journal of Medicinal Chemistry, 2008, 51(15):4359-4369.
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