Research Progress on Selective Multi-site Functionalization of Hydrocarbon Chains

doi:10.6023/cjoc202404010

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (11): 3273-3281.DOI: 10.6023/cjoc202404010 Previous Articles Next Articles

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碳氢链的选择性多位点官能化反应研究进展

王军威^a^,^b, 刘慧康^b, 杨泽华^a^,^*(), 吴正兴^b^,^*(), 张万斌^b^,^*()

a 南华大学衡阳医学院药学院药物药理研究所湖南衡阳 421001
b 上海交通大学化学化工学院上海市手性药物分子工程重点实验室上海 200240

收稿日期:2024-04-09 修回日期:2024-05-14 发布日期:2024-05-23
基金资助:
国家自然科学基金(21831005); 国家自然科学基金(21991112); 湖南省自然科学基金(2023JJ30500)

Research Progress on Selective Multi-site Functionalization of Hydrocarbon Chains

Junwei Wang^a^,^b, Huikang Liu^b, Zehua Yang^a,*(), Zhengxing Wu^b,*(), Wanbin Zhang^b,*()

a Institute of Pharmacy & Pharmacology, School of Pharmaceutical Science, Hengyang Medical School, University of South China, Hengyang, Hunan 421001
b Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received:2024-04-09 Revised:2024-05-14 Published:2024-05-23
Contact: *E-mail:yangzehua@usc.edu.cn;wzxtheway@sjtu.edu.cn;wanbin@sjtu.edu.cn
Supported by:
National Natural Science Foundation of China(21831005); National Natural Science Foundation of China(21991112); Natural Science Foundation of Hunan Province(2023JJ30500)

Selective functionalization of hydrocarbon chains is an important scientific problem in synthetic chemistry, and direct functionalization of easily available alkanes or alkenes is an ideal method for their efficient and high value-added conversion. Selective multi-site functionalization on the hydrocarbon chain (including C=C double bonds and C(sp³)—H bonds) can construct multiple chemical bonds in a one-step reaction, greatly improving the synthesis efficiency of compounds. For example, the multi-acetoxylation of hydrocarbon chains can be used for the efficient preparation of polyhydroxyl compounds, especially rare monosaccharides that are of great value in biology and medicine but rarely found in nature. The research progress in selective multi-site functionalization of hydrocarbon chains in recent years summarized from two aspects: multi-site functionalization of alkanes and multi-site functionalization of alkenes.

Key words: hydrocarbon chain, selectivity, multi-site, functionalization

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Junwei Wang, Huikang Liu, Zehua Yang, Zhengxing Wu, Wanbin Zhang. Research Progress on Selective Multi-site Functionalization of Hydrocarbon Chains[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3273-3281.

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Fig. & Tab. 15

Scheme 1. Selective functionalization of hydrocarbon chains

Scheme 2. Selective multi-functionalization of alkanes and alkenes

Scheme 3. Multi-bromination of amine-substituted alkanes

Scheme 4. Multi-acetoxylation of aryl- or amide-substituted alkanes

Scheme 5. Mechanism of multi-acetoxylation of alkanes

Scheme 6. Trifunctionalization of alkenes enabled by benzeneseleninic and trifluoroacetic anhydrides

Scheme 7. Palladium-catalyzed dehydrogenative diamination of alkenes

Scheme 8. Mechanism of palladium-catalyzed dehydrogenative diamination of alkenes

Scheme 9. Trifunctionalization of alkenes involving hydrazone radicals

Scheme 10. Mechanism of trifunctionalization of alkenes involving hydrazone radicals

Scheme 11. Trioxylation of α,β-unsaturated aldehydes

Scheme 12. Selective triboronation of alkenes catalyzed by cobalt

Scheme 13. Mechanism of selective triboronation of alkenes catalyzed by cobalt

Scheme 14. Dehydrogenative 1,2-diacetoxylation and 1,2,3-triacetoxylation of terminal alkenes

Scheme 15. Mechanism of dehydrogenative 1,2-diacetoxylation and 1,2,3-triacetoxylation of terminal alkenes

References 16

[1]	For selected reviews on activation of C—H bonds: (a) Aman H.; Chang R.; Ye J. Chin. J. Org. Chem. 2024, 44, 728 (in Chinese). pmid: 26566092
	(Hasil Aman 常瑞, 叶俊涛, 有机化学, 2024, 44, 728.) doi: 10.6023/cjoc202311032 pmid: 26566092
	(b) Liu N.; Cuan X.; Li H.; Duan X. Chin. J. Org. Chem. 2023, 43, 602 (in Chinese). pmid: 26566092
	(刘宁, 爨晓丹, 李慧, 段希焱, 有机化学, 2023, 43, 602.) doi: 10.6023/cjoc202207027 pmid: 26566092
	(c) Sinha S. K.; Guin S.; Maiti S.; Biswas J. P.; Porey S.; Maiti D. Chem. Rev. 2022, 122, 5682. pmid: 26566092
	(d) Wang P.-S.; Gong L.-Z. Acc. Chem. Res. 2020, 53, 2841. pmid: 26566092
	(e) He J.; Wasa M.; Chan K. S. L.; Shao Q.; Yu J.-Q. Chem. Rev. 2017, 117, 8754. pmid: 26566092
	(f) Hartwig J. F. J. Am. Chem. Soc. 2016, 138, 2. doi: 10.1021/jacs.5b08707 pmid: 26566092
[2]	For selected reviews on functionalization of alkenes: (a) Zhao Z.; Zhang F.; Wang D.; Deng L. Chin. J. Chem. 2023, 41, 3063. pmid: 21428440
	(b) Sun W.; Zhu S. Chin. J. Org. Chem. 2023, 43, 3339 (in Chinese). pmid: 21428440
	(孙伟, 朱守非, 有机化学, 2023, 43, 3339.) doi: 10.6023/cjoc202305016 pmid: 21428440
	(c) Zhang J.; Zhang C.; Mo N.; Luo J.; Chen L.; Liu W. Chin. J. Org. Chem. 2023, 43, 3098 (in Chinese). pmid: 21428440
	(张建涛, 张聪, 莫诺琳, 罗佳婷, 陈莲芬, 刘卫兵, 有机化学, 2023, 43, 3098.) doi: 10.6023/cjoc202303016 pmid: 21428440
	(d) Li S.; Shu X.; Wu L. Chin. J. Org. Chem. 2023, 43, 1751 (in Chinese). pmid: 21428440
	(李思达, 舒兴中, 吴立朋, 有机化学, 2023, 43, 1751.) doi: 10.6023/cjoc202212022 pmid: 21428440
	(e) Luo M.-J.; Xiao Q.; Li J.-H. Chem. Soc. Rev. 2022, 51, 7206. pmid: 21428440
	(f) Zhang M.; Ji Y.; Zhang C. Chin. J. Chem. 2022, 40, 1608. pmid: 21428440
	(g) Li X.; Tao P.; Cheng Y.; Hu Q.; Huang W.; Li Y.; Luo Z.; Huang G. Chin. J. Org. Chem. 2022, 42, 4169 (in Chinese). pmid: 21428440
	(李秀英, 陶萍芳, 程泳渝, 胡琼, 黄伟娟, 李芸, 罗志辉, 黄国保, 有机化学, 2022, 42, 4169.) doi: 10.6023/cjoc202204066 pmid: 21428440
	(h) Lu H.; Li B. Chin. J. Org. Chem. 2022, 42, 3167 (in Chinese). pmid: 21428440
	(陆候祥, 李必杰, 有机化学, 2022, 42, 3167.) doi: 10.6023/cjoc202207040 pmid: 21428440
	(i) Wickham L. M.; Giri R. Acc. Chem. Res. 2021, 54, 3415. pmid: 21428440
	(j) Kaur N.; Wu F.; Alom N.-E.; Ariyarathna J. P.; Saluga S. J.; Li W. Org. Biomol. Chem. 2019, 17, 1643. pmid: 21428440
	(k) Obligacion J. V.; Chirik P. J. Nat. Rev. Chem. 2018, 2, 15. doi: 10.1038/s41570-018-0001-2 pmid: 21428440
	(l) Margrey K. A.; Nicewicz D. A. Acc. Chem. Res. 2016, 49, 1997. pmid: 21428440
	(m) Mann S. E.; Benhamou L.; Sheppard T. D. Synthesis 2015, 47, 3079. pmid: 21428440
	(n) McDonald R. I.; Liu G.; Stahl S. S. Chem. Rev. 2011, 111, 2981. doi: 10.1021/cr100371y pmid: 21428440
[3]	Ghosh S.; Lai D.; Hajra A. Org. Biomol. Chem. 2020, 18, 7948.
[4]	Elshahawi S. I.; Shaaban K. A.; Kharel M. K.; Thorson J. S. Chem. Soc. Rev. 2015, 44, 7591. doi: 10.1039/c4cs00426d pmid: 25735878
[5]	Castillo E. D.; Martínez M. D.; Bosnidou A. E.; Duhamel T.; O’Broin C. Q.; Zhang H.; Escudero-Adán E. C.; Martínez- Belmonte M.; Muñiz K. Chem.-Eur. J. 2018, 24, 17225.
[6]	Shen T.; Li Y.-L.; Ye K.-Y.; Lambert T. H. Nature 2023, 614, 275.
[7]	Kutateladze A. G.; Kice J. L.; Kutateladze T. G. J. Org. Chem. 1993, 58, 995.
[8]	Wang B.; Du H.; Shi Y. Angew. Chem., Int. Ed. 2008, 47, 8224.
[9]	Duan X.-Y.; Yang X.-L.; Fang R.; Peng X.-X.; Yu W.; Han B. J. Org. Chem. 2013, 78, 10692.
[10]	Chen J. S.; Abeykoon G. A. Org. Lett. 2015, 17, 6050.
[11]	Zhao Y.; Ge S. Angew. Chem., Int. Ed. 2022, 61, e202116133.
[12]	Zhang L.; Huang Z. J. Am. Chem. Soc. 2015, 137, 15600. doi: 10.1021/jacs.5b11366 pmid: 26651355
[13]	Hu J.; Zhao Y.; Shi Z. Nat. Catal. 2018, 1, 860.
[14]	Wu Z.; Meng J.; Liu H.; Li Y.; Zhang X.; Zhang W. Nat. Chem. 2023, 15, 988.
[15]	Ge Q.; Meng J.; Liu H.; Yang Z.; Wu Z.; Zhang W. Chin. J. Chem. 2022, 40, 2269.
[16]	Hu S.-P.; Gao C.-H.; Liu T.-M.; Miao B.-Y.; Wang H.-C.; Yu W.; Han B. Angew. Chem., Int. Ed. 2024, e202400168.

碳氢链的选择性多位点官能化反应研究进展

Research Progress on Selective Multi-site Functionalization of Hydrocarbon Chains

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