Visible-Light-Promoted Direct Trifluoromethylation of Tryptophan-Containing Oligapeptides with YlideFluor

doi:10.6023/cjoc202209018

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1517-1524.DOI: 10.6023/cjoc202209018 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑

ARTICLES

可见光促进的含色氨酸寡肽与YlideFluor试剂的直接三氟甲基化反应研究

刘静^a, 郝健^a^,^*(), 沈其龙^b^,^*()

a 上海大学化学系上海 200444
b 中国科学院上海有机化学研究所有机氟化学重点实验室上海 200032

收稿日期:2022-09-14 修回日期:2022-11-14 发布日期:2022-11-21
通讯作者: 郝健, 沈其龙
基金资助:
国家重点研发计划(2021YFF0701700)

Visible-Light-Promoted Direct Trifluoromethylation of Tryptophan-Containing Oligapeptides with YlideFluor

Jing Liu^a, Jian Hao^a(), Qilong Shen^b()

a Department of Chemistry, Shanghai University, Shanghai 200444
b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2022-09-14 Revised:2022-11-14 Published:2022-11-21
Contact: Jian Hao, Qilong Shen
Supported by:
National Key Research and Development Program of China(2021YFF0701700)

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Abstract

A photosensitizer-free visible-light-promoted method for site-selective trifluoromethylation of tryptophan- containing oligopeptides using YlideFluor as the trifluoromethyl radical source under mild conditions was developed. Mechanistic studies showed that a donor-acceptor between 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and YlideFluor is generated. Upon irradiation with blue LEDs, the S—CF₃ bond in the adduct undergoes homolytic cleavage to give trifluoromethyl radical, which attacks the electron-rich C-2 position of the indole moiety in the tryptophan-containing oligopeptide.

Key words: fluorine, trifluoromethyl, tryptophan, oligapeptide, visible light

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Jing Liu, Jian Hao, Qilong Shen. Visible-Light-Promoted Direct Trifluoromethylation of Tryptophan-Containing Oligapeptides with YlideFluor[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1517-1524.

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Fig. & Tab. 5

References 18

[1]	(a) Erak, M.; Bellmann-Sickert, K.; Els-Heindl, S.; Beck-Sickinger, A. G. Bioorg. Med. Chem. 2018, 26, 2759. doi: 10.1016/j.bmc.2018.01.012 pmid: 31804810
	(b) Kaspar, A. A.; Reichert, J. M. Drug Discovery Today 2013, 18, 807. doi: 10.1016/j.drudis.2013.05.011 pmid: 31804810
	(c) Malonis, R. J.; Lai, J. R.; Vergnolle, O. Chem. Rev. 2020, 120, 3210. doi: 10.1021/acs.chemrev.9b00472 pmid: 31804810
[2]	(a) Reddy, B..Jow T.; Hantash, B. M. Exp. Dermatol. 2012, 21, 563. doi: 10.1111/j.1600-0625.2012.01528.x
	(b) Ji, Y.-J.; Qiao, H.-Z.; He, J.-Y.; Li, W.-D.; Chen, R.; Wang, J.-J.; Wu, L.; Hu, R.-F.; Duan, J.-N.; Chen, Z.-P. J. Drug Target. 2017, 25, 597. doi: 10.1080/1061186X.2017.1309044
[3]	deGruyter, J. N.; Malins, L. R.; Baran, P. S. Biochemistry 2017, 56, 3863. doi: 10.1021/acs.biochem.7b00536 pmid: 28653834
[4]	Chalker, J. M.; Bernardes, G. J. L.; Lin, Y. A.; Davis, B. G. Chem. Asian J. 2009, 4, 630. doi: 10.1002/asia.v4:5
[5]	(a) Ban, H.; Gavrilyuk, J.; Barbas III, C. F. J. Am. Chem. Soc. 2010, 132, 1523. doi: 10.1021/ja909062q
	(b) Ban, H.; Nagano, M.; Gavrilyuk, J.; Hakamata, W.; Inokuma, T.; Barbas III, C. F. Bioconjugate Chem. 2013, 24, 520. doi: 10.1021/bc300665t
[6]	Ohata, J.; Minus, M. B.; Abernathy, M. E.; Ball, Z. T. J. Am. Chem. Soc. 2016, 138, 7472. doi: 10.1021/jacs.6b03390 pmid: 27249339
[7]	(a) Ruiz-Rodriguez, J.; Albericio, F.; Lavilla, R. Chem.-Eur. J. 2010, 16, 1124. doi: 10.1002/chem.200902676 pmid: 20013969
	(b) Seki, Y.; Ishiyama, T.; Sasaki, D.; Abe, J.; Sohma, Y.; Oisaki, K.; Kanai, M. J. Am. Chem. Soc. 2016, 138, 10798. doi: 10.1021/jacs.6b06692 pmid: 20013969
	(c) Hansen, M. B.; Hubalek, F.; Skrydstrup, T.; Hoeg-Jensen, T. Chem.-Eur. J. 2016, 22, 1572. doi: 10.1002/chem.201504462 pmid: 20013969
	(d) Ruan, Z.; Sauermann, N.; Manoni, E.; Ackermann, L. Angew. Chem., Int. Ed. 2017, 56, 3172. doi: 10.1002/anie.201611118 pmid: 20013969
[8]	Guerrero, I.; Correa, A. Asian J. Org. Chem. 2020, 9, 898. doi: 10.1002/ajoc.v9.6
[9]	(a) Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525. doi: 10.1021/cr60274a001
	(b) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165. doi: 10.1021/cr00002a004
	(c) Qing, F.-L.; Liu, X.-Y.; Ma, J.-A.; Shen, Q.; Song, Q.-L.; Tang, P.-P. CCS Chem. 2022, 4, 2518. doi: 10.31635/ccschem.022.202201935
[10]	Wang, Y.-X.; Wang, J.-H.; Li, G.-X..He G. ; Chen, G. Org. Lett. 2017, 19, 1442. doi: 10.1021/acs.orglett.7b00375
[11]	Imiolek, M.; Karunanithy, G.; Ng, W.-L.; Baldwin, A. J.; Gourverneur, V.; Davis, B. G. J. Am. Chem. Soc. 2018, 140, 1568. doi: 10.1021/jacs.7b10230
[12]	Ding, B.; Weng, Y.; Liu, Y.-Q.; Song, C.-L.; Yin, L.; Yuan, J.-F.; Ren, Y.-R.; Lei, A.-W.; Chiang, C.-W. Eur. J. Org. Chem. 2019, 7596.
[13]	Guerrero, I.; Correa, A. Org. Lett. 2020, 22, 1754. doi: 10.1021/acs.orglett.0c00033 pmid: 32052977
[14]	Kee, C. W.; Tack, O.; Guibbal, F.; Wilson, T. C.; Iseneggar, P. G.; Imiolek, M.; Verhoog, S.; Tilby, M.; Boscutti, G.; Ashworth, S.; Chupin, J.; Kashani, R.; Poh, A. W. J.; Sosabowski, J. K.; Macholl, S.; Plisson, C.; Cornelissen, B.; Willis, M. C.; Passchier, J.; Davis, B. G.; Gouverneur, V. J. Am. Chem. Soc. 2020, 142, 1180. doi: 10.1021/jacs.9b11709
[15]	Liu, Y.-F.; Shao, X.-X.; Lu, L.; Shen, Q. Org. Lett. 2015, 17, 2752. doi: 10.1021/acs.orglett.5b01170
[16]	(a) Liu, Y.-F.; Ling, Y.-J.; Ge, H.-M.; Lu, L.; Shen, Q. Chin. J. Chem. 2021, 39, 1667. doi: 10.1002/cjoc.v39.6
	(b) Yao, R.-C.; Ling, Y.-J.; Chen, W.-B.; Lu, L.; Shen, Q. Org. Process Res. Dev. 2022, 26, 299. doi: 10.1021/acs.oprd.1c00381
[17]	(a) Ge, H.-M.; Shen, Q. Org. Chem. Front. 2019, 10, 2205.
	(b) Ge, H.-M.; Wu, B.-T.; Liu, Y.-F.; Wang, H.-Y.; Shen, Q. ACS Catal. 2020, 10, 12414. doi: 10.1021/acscatal.0c03776
	(c) Yao, R.-C.; Chen, W.-B.; Shen, Q. Chin. J. Org. Chem. 2021, 41, 2684. (in Chinese) doi: 10.6023/cjoc202103004
	(姚瑞超, 陈文博, 沈其龙, 有机化学, 2021, 41, 2684.) doi: 10.6023/cjoc202103004
[18]	Cheng, Y. Z.; Yuan, X. G.; Ma, J.; Yu, S. Y. Chem.-Eur. J. 2015, 21, 8355. doi: 10.1002/chem.v21.23

Entry	Additive	Ylidefluor/equiv.	Yield^a/%
1	TEMPO	1.22	2
2	Under air	0.32	18
3	BHT		42
4	1,4-Dinitrobenzene		50

Entry	Additive	Ylidefluor/equiv.	Yield^a/%
1	TEMPO	1.22	2
2	Under air	0.32	18
3	BHT		42
4	1,4-Dinitrobenzene		50

可见光促进的含色氨酸寡肽与YlideFluor试剂的直接三氟甲基化反应研究

Visible-Light-Promoted Direct Trifluoromethylation of Tryptophan-Containing Oligapeptides with YlideFluor

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Entry	Solvent	Base	Light	Time/h	Yield/%
1	DMSO	DBU	Blue	12	60
2	DMSO	DMAP	Blue	12	27
3	DMSO	DIPEA	Blue	12	25
4	DMSO	Cs₂CO₃	Blue	12	18
5	DMSO	NaHCO₃	Blue	12	41
6	CH₃CN	DBU	Blue	12	29
7	DMF	DBU	Blue	12	28
8	DMAc	DBU	Blue	12	22
9	NMP	DBU	Blue	12	18
10	Acetone	DBU	Blue	12	46
11	H₂O	DBU	Blue	12	33
12	THF	DBU	blue	12	2
13	CH₂Cl₂	DBU	Blue	12	45
14	DMSO	DBU	White	12	54
15	DMSO	DBU	Purple	12	56
16	DMSO	DBU		12	46
17	DMSO	DBU	Blue	6	54
18	DMSO	DBU	Blue	9	58
19	DMSO		Blue	12	34
20^c	DMSO			12

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