SIOC English
有机化学
高级检索

有机化学 >

2023 , Vol. 43 >Issue 10: 3580 - 3589

DOI: https://doi.org/10.6023/cjoc202303030

综述与进展

硅基羧酸在有机合成中的应用进展

  • 郭广青 ,
  • 练仲
展开
  • a 四川大学华西医院 生物治疗国家重点实验室 成都 610041
    b 四川大学华西药学院 成都 610041

收稿日期: 2023-03-21

  修回日期: 2023-04-20

  网络出版日期: 2023-05-15

基金资助

国家自然科学基金(21901168); “国家青年千人计划”、四川省科技计((2021YJ0395); 四川大学华西医院1.3.5优秀学科建设资助项目

收起

Application Progress of Silyl Carboxylic Acid in Organic Synthesis

  • Guangqing Guo ,
  • Zhong Lian
Expand
  • a State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041
    b West China School of Pharmacy, Sichuan University, Chengdu 610041
*E-mail:

Received date: 2023-03-21

  Revised date: 2023-04-20

  Online published: 2023-05-15

Supported by

National Natural Science Foundation of China(21901168); “1000-Youth Talents Plan”, the Sichuan Science and Technology Program(2021YJ0395); “1.3.5 Project for Disciplines of Excellence, West China Hospital, Sichuan University”

Fold

摘要

羧酸在有机体基本生命过程中起着非常重要的作用, 同时在有机合成化学领域也是一种功能强大的合成砌块. 因此, 无论是天然存在还是人工合成的羧酸都已经从多个方面被广泛研究. 硅基羧酸, 作为羧酸的类似物, 因其独特的理化性质和潜在的反应性吸引了化学家们的关注. 综述了硅基羧酸在插羰偶联反应、硅自由基反应以及酯化反应中的应用. 硅基羧酸作为硅自由基前体。

关键词： 硅基羧酸; 一氧化碳; 羰基化反应; 硅基自由基前体

本文引用格式

郭广青 , 练仲 . 硅基羧酸在有机合成中的应用进展[J]. 有机化学, 2023 , 43(10) : 3580 -3589 . DOI: 10.6023/cjoc202303030

Abstract

Carboxylic acids play important roles in basic life processes within organisms, and are powerful building blocks in the field of organic synthesis. Therefore, natural or artificial carboxylic acids have been studied from a variety of viewpoints. Silyl carboxylic acids, as analogues of carboxylic acids, are highly attractive due to their unique physical and chemical properties as well as their potential reactivity. The applications of silyl carboxylic acids in the carbonyl coupling reactions, silyl radical reactions and esterification are summarized.

Key words： silyl carboxylic acid; carbon monoxide; carbonylation reaction; silyl radical precursor

参考文献

[1]
Li L.; Wei Y.-L.; Xu L.-W. Synlett 2020, 31, 21.
[2]
Andrus M. B.; Liu J.; Meredith E. L. Tetrahedron Lett. 2003, 44, 4819.
[3]
Liu K. M.; Zhang R.; Duan X.-F. Org. Biomol. Chem. 2016, 14, 1593.
[4]
Wang Y.-F.; Pan J.; Dong J.-J.; Yu C.-X.; Li T.-J.; Wang X.-S.; Shen S.; Yao C.-S. J. Org. Chem. 2017, 82, 1790.
[5]
Shimizu M.; Hirano K.; Satoh T.; Miura M. J. Org. Chem. 2009, 74, 3478.
[6]
Ruso J. S.; Rajendiran N.; Kumaran R. S. Tetrahedron Lett. 2014, 55, 2345.
[7]
Wooley K. L.; Fréchet J. M.; Hawker C. J. Polymer 1994, 35, 4489.
[8]
Akagawa K.; Kudo K. Chem. Commun. 2017, 53, 8645.
[9]
Benkeser R. A.; Severson R. G. J. Am. Chem. Soc. 1951, 73, 1424.
[10]
Friis S. D.; Taaning R. H.; Lindhardt A. T.; Skrydstrup T. J. Am. Chem. Soc. 2011, 133, 18114.
[11]
Hernández D.; Mose R.; Skrydstrup T. Org. Lett. 2011, 13, 732-735.
[12]
Markovi? M.; Lopatka P.; Koó? P.; Gracza T. Org. Lett. 2015, 17, 5618.
[13]
Mondal K.; Halder P.; Gopalan G.; Sasikumar P.; Radhakrishnan K. V.; Das P. Org. Biomol. Chem. 2019, 17, 5212.
[14]
Jafarpour F.; Rashidi-Ranjbar P.; Kashani A. O. J. Org. Chem. 2011, 76, 21282.
[15]
Gehrtz P. H.; Hirschbeck V.; Fleischer I. Chem. Commun. 2015, 51, 12574.
[16]
Friis S. D.; Anders T. L.; Skrydstrup T. Acc. Chem. Res. 2016, 49, 594.
[17]
Cao J.; Zheng Z.-J.; Xu Z.; Xu L.-W. Coord. Chem. Rev. 2017, 336, 43.
[18]
Gilman H.; Brook A. G. J. Am. Chem. Soc. 1955, 77, 2322.
[19]
Brook A. G. Acc. Chem. Res. 1974, 7, 77.
[20]
Friis S. D.; Anders T. L.; Skrydstrup T. Org. Lett. 2013, 15, 1378.
[21]
Friis S. D.; Skrydstrup T.; Buchwald S. L. Org. Lett. 2014, 16, 4296.
[22]
Lian Z.; Friis S. D.; Anders T. L.; Skrydstrup T. Synlett 2014, 25, 1241.
[23]
Makarov I. S.; Kuwahara T.; Jusseau X.; Ryu I.; Anders T. L.; Skrydstrup T. J. Am. Chem. Soc. 2015, 137, 14043.
[24]
Laursen S. R.; Jensen M. T.; Lindhardt A. T.; Jacobsen M. F.; Skrydstrup T. Eur. J. Org. Chem. 2016, 2016, 1881.
[25]
Skogh A.; Friis S. D.; Skrydstrup T.; Sandstr?m A. Org. Lett. 2017, 19, 2873.
[26]
Neumann K. T.; Donslund A. S.; Andersen T. L.; Nielsen D. U.; Skrydstrup T. Chem.-Eur. J. 2018, 24, 14946.
[27]
Pedersen S. K.; Gudmundsson H. G.; Nielsen D. U.; Donslund B. S.; Hammersh?j H. C. D.; Daasbjerg K.; Skrydstrup T. Nat. Catal. 2020, 3, 843.
[28]
Brennfu?hrer A.; Neumann H.; Beller M. Angew. Chem., Int. Ed. 2009, 48, 4114.
[29]
Martinelli J. R.; Clark T. P.; Watson D. A.; Munday R. H.; Buchwald S. L. Angew. Chem., Int. Ed. 2007, 46, 8460.
[30]
Munday R. H.; Martinelli J. R.; Buchwald S. L. J. Am. Chem. Soc. 2008, 130, 2754.
[31]
Grigg R.; Mutton S. P. Tetrahedron. 2010, 66, 5515.
[32]
Friis S. D.; Skrydstrup T.; Buchwald S. L. Org. Lett. 2014, 16, 4296.
[33]
Xu T.; Alper H. J. Am. Chem. Soc. 2014, 136, 16970.
[34]
Andersen T. L.; Friis S. D.; Audrain H.; Nordeman P.; Antoni G.; Skrydstrup T. J. Am. Chem. Soc. 2015, 137, 1548.
[35]
Cornilleau T.; Audrain H.; Guillemet A.; Hermange P.; Fouquet E. Org. Lett. 2015, 17, 354.
[36]
Cornilleau T.; Simonsen M.; Vang M.; Taib-Maamar N.; Dessolin J.; Audrain H.; Hermange P.; Fouquet E. Bioconjugate Chem. 2017, 28, 2887.
[37]
Tabey A.; Audrain H.; Fouquet E.; Hermange P. Chem. Commun. 2019, 55, 7587.
[38]
Christine T.; Tabey A.; Cornilleau T.; Fouquet E.; Hermange P. Tetrahedron. 2019, 75, 130765.
[39]
Cormier M., Tabey A., Christine T., Audrain H., Fouquet E., Hermange P. Dalton Trans. 2021, 50, 10608.
[40]
Li X.; Xu J. ; Kramer S.; Skrydstrup T.; Lian Z. Adv. Synth. Catal. 2020, 362, 4078.
[41]
Li X.; Zhang X.-M.; Xiong B.-J.; Lian Z. J. Org. Chem. 2023, 88, 5226.
[42]
Werkmeister S.; Junge K.; Wendt B.; Alberico E.; Jiao H.; Baumann W.; Junge H.; Gallou F.; Beller M. Angew. Chem., Int. Ed. 2014, 53, 8722.
[43]
Bornschein C.; Werkmeister S.; Wendt B.; Jiao H.; Alberico E.; Baumann W.; Junge H.; Junge K.; Beller M. Nat. Commun. 2014, 5, 4111.
[44]
Rezayee N. M.; Samblanet D. C.; Sanford M. S. ACS Catal. 2016, 6, 6377.
[45]
Alberico E.; Sponholz P.; Cordes C.; Nielsen M.; Drexler H.-J.; Baumann W.; Junge H.; Beller M. Angew. Chem., Int. Ed. 2013, 52, 14162.
[46]
Chakraborty S.; Brennessel W. W.; Jones W. D. J. Am. Chem. Soc. 2014, 136, 8564.
[47]
Anke F.; Han D.; Klahn M.; Spannenberg A.; Beweries T. Dalton Trans. 2017, 46, 6843.
[48]
Sun H.-W.; Ahrens A.; Kristensen K. S.; Gausas L.; Donslund S. B.; Skrydstrup T. Org. Process Res. Dev. 2021, 25, 2300.
[49]
Igawa K.; Kokan N.; Tomooka K. Angew. Chem., Int. Ed. 2010, 49, 728.
[50]
Liang J.-Y.; Shen S.-J.; Xu X.-H.; Fu Y.-L. Org. Lett. 2018, 20, 6627.
[51]
Zhao Z.-J; He B.-R.; Tang B.-Z. Chem. Sci. 2015, 6, 5347.
[52]
Remond C.; Martin J.; Martinez F. Cavelier, Chem. Rev. 2016, 116, 11654.
[53]
Chatgilialoglu C. Chem. Rev. 1995, 95, 1229.
[54]
Xu N.-X; Li B.-X.; Wang C.; Uchiyama M. Angew. Chem., Int. Ed. 2020, 59, 10639.
Options
文章导航

/

〈 〉