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2023 , Vol. 43 >Issue 9: 3055 - 3066

DOI: https://doi.org/10.6023/cjoc202303036

综述与进展

光诱导醇的直接脱羟基衍生化研究进展

  • 鄢伯钰 ,
  • 吴阶良 ,
  • 邓金飞 ,
  • 陈丹 ,
  • 叶秀深 ,
  • 姚秋丽
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  • a 遵义医科大学药学院 贵州遵义 563000
    b 中国科学院青海盐湖研究所 西宁 810008

收稿日期: 2023-03-23

  修回日期: 2023-05-04

  网络出版日期: 2023-06-07

基金资助

国家自然科学基金(22161053); 国家自然科学基金(21801261); 贵州省科技厅([2020]1Z003); 贵州省教育厅(20195201900); 遵义医科大学优秀青年人才(18zy-003); 青海省千人计划资助项目

收起

Recent Progress in Light-Driven Direct Dehydroxylation and Derivation of Alcohols

  • Boyu Yan ,
  • Jieliang Wu ,
  • Jinfei Deng ,
  • Dan Chen ,
  • Xiushen Ye ,
  • Qiuli Yao
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  • a College of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000
    b Qinghai Institute of Salt Lakes, Chinese Academy of Sciences, Xi'ning 810008
* E-mail:

Received date: 2023-03-23

  Revised date: 2023-05-04

  Online published: 2023-06-07

Supported by

National Natural Science Foundation of China(22161053); National Natural Science Foundation of China(21801261); Guizhou Science and Technology Department([2020]1Z003); Guizhou Education Department(20195201900); Zunyi Medical University Outstanding Young Talents(18zy-003); Thousand Talents Plan of Qinghai Province

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摘要

由于Csp3—O键键能大的特点, 传统还原裂解醇类的方法多涉及间接的活化过程, 在温和条件下对醇Csp3—O键直接裂解是一个巨大的挑战. 近年来通过光诱导条件直接对其裂解进行脱羟基还原、脱羟基衍生化的策略取得了重大的突破, 这些策略相较于传统方法不需要预活化步骤, 也能避免传统当量氧化还原剂的使用, 具有更好的原子经济性、步骤经济性以及氧化还原经济性. 该主题综述文献较少, 在此重点综述了光诱导下醇Csp3—O键直接裂解还原及衍生化的进展, 从而进一步推动该领域的蓬勃发展.

关键词： 醇; 还原; 烷基化; 脱羟基; 光化学

本文引用格式

鄢伯钰 , 吴阶良 , 邓金飞 , 陈丹 , 叶秀深 , 姚秋丽 . 光诱导醇的直接脱羟基衍生化研究进展[J]. 有机化学, 2023 , 43(9) : 3055 -3066 . DOI: 10.6023/cjoc202303036

Abstract

Conventional methods for the reduction of alcohols mainly deal with the indirect cleavages of Csp3—O bond involving tedious activated steps. In contrast, the more straightforward direct reduction of naturally abundant aliphatic alcohols to alkanes or other reductive derivatives poses a challenge to organic chemists due to the inherently stable and less reactive Csp3—O bond. The development of direct reductive strategies induced by light is of utmost importance due to their atom economy, step economy and redox economy, and many progresses have been made in this area these years. However, very few reviews on this topic has been reported so far. Herein, the recent progress in the light-driven direct deoxygenation of alcohols with emphasis on important advances last ten years is reviewed, which is expected to further promote the vigorous development of this field.

Key words： alcohols; reduction; alkylation; dehydroxylation; photochemistry

参考文献

[1]
(a) Modak A.; Maiti D. Org. Biomol. Chem. 2016, 14, 21.
[1]
(b) Anwar K.; Merkens K.; Aguilar Troyano F. J.; Gómez-Suárez A. Eur. J. Org. Chem. 2022, 2022, 202200330.
[2]
Haynes W. M. Handbook of Chemistry and Physics, 93rd ed., CRC Press, 2012.
[3]
(a) Ren L.; Ran M.; He J.; Qian Y.; Yao Q. Chin. J. Org. Chem. 2019, 39, 1583. (in Chinese)
[3]
(任林静, 冉茂刚, 何佳芯, 钱燕, 姚秋丽, 有机化学, 2019, 39, 1583.)
[3]
(b) Leifert D.; Studer A. Angew. Chem., Int. Ed. 2020, 59, 74.
[3]
(c) Yan B.; Zhou Y.; Wu J.; Ran M.; Li H.; Yao Q. Org. Chem. Front. 2021, 8, 5244.
[3]
(d) Meng J.; Zhou Y.; Gu J.; Deng J.; Zheng Q.; Ye X.; Yao Q. J. Org. Chem. 2023, 88, 1855.
[3]
(e) Wu J.; Yan B.; Meng J.; Yang E.; Ye X.; Yao Q. Org. Biomol. Chem. 2022, 20, 8559.
[4]
Herrmann J. M.; K?nig B. Eur. J. Org. Chem. 2013, 2013, 7017.
[5]
(a) Mao G.; Jia B.; Wang C. Chin. J. Org. Chem. 2015, 35, 284. (in Chinese)
[5]
(毛国梁, 贾冰, 王从洋, 有机化学, 2015, 35, 284.)
[5]
(b) Li C.; Zhang Q.; Fu Y. Acta Chim. Sinica 2018, 76, 501. (in Chinese)
[5]
(李翠, 张琪, 傅尧, 有机化学, 2018, 76, 501.)
[5]
(c) Pichon M. M.; Hazelard D.; Compain P. Eur. J. Org. Chem. 2019, 2019, 6320.
[6]
(a) Liu F.; Jiang H. J.; Zhou Y.; Shi Z. J. Chin. J. Chem. 2020, 38, 855.
[6]
(b) Qiu Z.; Li C. J. Chem. Rev. 2020, 120, 10454.
[7]
Gao J.; Feng J.; Du D. Chem. Asian J. 2020, 15, 3637.
[8]
Nguyen J. D.; Reiss B.; Dai C.; Stephenson C. R. Chem. Commun. 2013, 49, 4352.
[9]
Uranga J. G.; Chiosso A. F.; Santiago A. N. RSC Adv. 2013, 3, 11493.
[10]
McCallum T.; Slavko E.; Morin M.; Barriault L. Eur. J. Org. Chem. 2015, 2015, 81.
[11]
Takada Y.; Caner J.; Kaliyamoorthy S.; Naka H.; Saito S. Chem. Eur. J. 2017, 23, 18025.
[12]
Stache E. E.; Ertel A. B.; Tomislav R.; Doyle A. G. ACS Catal. 2018, 8, 11134.
[13]
Cao D.; Chen Z.; Lv L.; Zeng H.; Peng Y.; Li C. J. iScience 2020, 23, 101419.
[14]
Ran C.-K.; Niu Y.-N.; Song L.; Wei M.-K.; Cao Y.-F.; Luo S.-P.; Yu Y.-M.; Liao L.-L.; Yu D.-G. ACS Catal. 2022, 12, 18.
[15]
Li W. D.; Wu Y.; Li S. J.; Jiang Y. Q.; Li Y. L.; Lan Y.; Xia J. B. J. Am. Chem. Soc. 2022, 144, 8551.
[16]
Fan Z.; Chen S.; Zou S.; Xi C. ACS Catal. 2022, 12, 2781.
[17]
Dai C.; Narayanam J. M.; Stephenson C. R. Nat. Chem. 2011, 3, 140.
[18]
Xue W.; Yuan X.; Cheng S.; Shi Y. Synthesis 2014, 46, 331.
[19]
Zhao Y.; Antonietti M. ChemPhotoChem 2018, 2, 720.
[20]
Mohite A. R.; Phatake R. S.; Dubey P.; Agbaria M.; Shames A. I.; Lemcoff N. G.; Reany O. J. Org. Chem. 2020, 85, 12901.
[21]
Tomar P.; Braun T.; Kemnitz E. Chem. Commun. 2018, 54, 9753.
[22]
Barreiro E. J.; Kummerle A. E.; Fraga C. A. Chem. Rev. 2011, 111, 5215.
[23]
(a) Stermitz F. R.; Seiber R. P.; Nicodem D. E. J. Org. Chem. 1968, 33, 1136.
[23]
(b) Stermitz F. R.; Wei C. C.; O'Donnell C. M. J. Am. Chem. Soc. 1970, 92, 2745.
[23]
(c) Takeuchi F.; Sugiyama T.; Fujimori T.; Seki K.; Harada Y.; Sugimori A. Bull. Chem. Soc. Jpn 1974, 47, 1245.
[23]
(d) Mariano P. S. Tetrahedron 1983, 39, 3845.
[23]
(e) Padwa A. Chem. Rev. 2002, 77, 37.
[24]
Jin J.; MacMillan D. W. C. Nature 2015, 525, 87.
[25]
Nacsa E. D.; MacMillan D. W. C. J. Am. Chem. Soc. 2018, 140, 3322.
[26]
Dong Z.; MacMillan, D. W. C. Nature 2021, 598, 451.
[27]
Sakai H. A.; MacMillan D. W. C. J. Am. Chem. Soc. 2022, 144, 6185.
[28]
Intermaggio N. E.; Millet A.; Davis D. L.; MacMillan D. W. C. J. Am. Chem. Soc. 2022, 144, 11961.
[29]
Wang J. Z.; Sakai H. A.; MacMillan D. W. C. Angew. Chem., Int. Ed. 2022, 61, e202207150.
[30]
Guo H. M.; Wu X. Nat. Commun. 2021, 12, 5365.
[31]
Guo H. M.; He B. Q.; Wu X. Org. Lett. 2022, 24, 3199.
[32]
Zhang W.; Ning S.; Li Y.; Wu X. Chem. Commun. 2022, 58, 12843.
[33]
Bao W. H.; Wu X. J. Org. Chem. 2023, 88, 3975.
[34]
Tan C. Y.; Kim M.; Park I.; Kim Y.; Hong S. Angew. Chem., Int. Ed. 2022, 61, e202213857.
[35]
Liu W.; Yang X.; Zhou Z.-Z.; Li C.-J. Chem 2017, 2, 688.
[36]
Zhang F.; Hou H.; Xu X.; Chen Z.; Ke F. Chin. J. Org. Chem. 2021, 41, 833. (in Chinese)
[36]
(张帆, 侯慧青, 许秀枝, 陈志涛, 柯方, 有机化学, 2021, 41, 833.)
[37]
Xie Z.; Lan J.; Zhu H.; Lei G.; Jiang G.; Le Z. Chin. Chem. Lett. 2021, 32, 1427.
[38]
Wang M.; Ren J.; Xiao Q.; Song A.; Yu S.; Wang R.; Xing L. Catal. Lett. 2023, doi:10.1007/s10562-022-04266-y.
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