Influence of C—F…H—X Interactions on Organic Reactions

doi:10.6023/A18080360

Acta Chim. Sinica ›› 2018, Vol. 76 ›› Issue (12): 925-939.DOI: 10.6023/A18080360 Previous Articles Next Articles

Special Issue: 有机氟化学

Review

C―F…H―X相互作用在有机反应中的影响

郝永佳^a, 余金生^b, 周英^a, 王欣^d, 周剑^b,a,c

a. 贵阳中医学院药学院贵阳 550025;
b. 绿色化学与化工过程绿色化上海市重点实验室上海分子治疗与新药创制工程技术研究中心华东师范大学化学与分子工程学院上海 200062;
c. 金属有机化学国家重点实验室中国科学院上海有机化学研究所上海 200032;
d. 四川大学化学学院成都 610064

投稿日期:2018-08-31 发布日期:2018-10-18
通讯作者: 周剑,E-mail:jzhou@chem.ecnu.edu.cn,Tel.:021-62234560,Fax:021-62234560 E-mail:jzhou@chem.ecnu.edu.cn
作者简介:郝永佳,男,汉族,1987年生.2016年6月博士毕业于华东理工大学,化学生物技术与工程专业.2018年加入贵阳中医学院药学院,研究方向为(天然)药物化学、药物合成,目前主要从事生物活性分子的设计、合成及活性研究工作;余金生,男,1988年生于江西九江.2011年本科毕业于江西师范大学,随后加入华东师范大学周剑教授课题组,并于2016年获得有机化学博士学位.2017年初至今在日本微生物化学研究所Shibasaki教授小组进行JSPS博士后研究,主要从事重要手性砌块的不对称催化合成研究;周英,博士,贵阳中医学院药学院教授,博士生导师,教育部新世纪优秀人才,西南药食两用资源开发利用技术国家地方联合工程中心主任.1998年博士毕业于北京大学医学部(原北京医科大学),2003年至2005年在美国肯塔基大学医学中心做博士后研究.主要从事中药民族药研究以及药物优势骨架导向的多样性原创小分子化合物设计、合成及其生物活性研究.
基金资助:
项目受国家自然科学基金（Nos.21472049，81660576）与贵州省药食同源植物资源开发工程技术研究中心（黔科合G字[2015]4001号）资助.

Influence of C—F…H—X Interactions on Organic Reactions

Hao Yong-Jia^a, Yu Jin-Sheng^b, Zhou Ying^a, Wang Xin^d, Zhou Jian^b,a,c

a. College of Pharmacy, Guiyang University of Chinese Medicine, Guiyang 550025;
b. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062;
c. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032;
d. College of Chemistry, Sichuan University, Chengdu 610064

Received:2018-08-31 Published:2018-10-18
Contact: 10.6023/A18080360 E-mail:jzhou@chem.ecnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21472049, 81660576) and Guizhou engineering research center for the exploitation and utilization technology of medicine and food dual-use resources.

Although the debate on whether or not C―F bonds can function as H-bond acceptors lasted for tens of years, dating back to 1939 when Pauling pointed out in The Nature of the Chemical Bond that C-F bonds do not have significant power to act as proton acceptors in the formation of hydrogen bonds, more and more evidences support the existence of C―F…H―X interactions, and in particular, C―F…H―O and C―F…H―N interactions cannot be ignored.Because the sum of the van der Waals radii of hydrogen and fluorine atoms is reported to be around as 2.55 Å, C―F…H―X interactions may exist if the calculated distance of F…H is less than 2.50 Å. Strong C―F…H―X interactions may occur if the calculated distance is less than 2.30 Å and the F…H―X angle is greater than 120°.In 2011, we observed strong fluorine effects on the Strecker reaction of ketimines: while Schreiner's thiourea could catalyze the Strecker reaction of acetophenone derived ketimine using TMSCN, it was unable to mediate the corresponding reaction of analogy α-CF₃ or α-CF₂H ketimines. Theoretical calculations revealed that the C―F…H―N interactions between the C―F bond of fluorinated ketimines and thiourea played the key role. This is the first report on the influence of such subtle interactions on organic reactions. Since then, reports from our and other groups revealed various types of C―F…H―X interactions that may be present in the reaction course, to strongly influence the reactivity and selectivity. Although successful examples are still limited, these achievements have suggested that C―F…H―X interactions may exist between the substrate and the catalyst; the substrate and the solvent; different reaction partners, or engender in the transition state with the reaction intermediate. Importantly, known examples demonstrate it possible to harness C―F…H―X interactions to tune reactivity and/or selectivity, which are useful for new reaction development, as well as for the design of new catalysts. To provide reference and inspiration for researchers engaged in organic synthesis, especially the organic fluorine chemistry, we summarize in this review the recent advances in the study of the influences of C―F…H―X interactions on organic reactions.

Key words: C―F…H―X interaction, organic reaction, reactivity, selectivity

Cite this article

Hao Yong-Jia, Yu Jin-Sheng, Zhou Ying, Wang Xin, Zhou Jian. Influence of C—F…H—X Interactions on Organic Reactions[J]. Acta Chim. Sinica, 2018, 76(12): 925-939.

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C―F…H―X相互作用在有机反应中的影响

Influence of C—F…H—X Interactions on Organic Reactions

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