Blue Light Induced Insertion of Carbene into C(CO)—C Bonds of 1,3-Diones

doi:10.6023/cjoc202201045

Abstract

Visible light is an ideal “tool” for the green chemical synthesis. Visible light-induced reactions show such advantages as mild reaction conditions, simple equipments and less by-products. Therefore, it has gradually become an important method in organic synthesis. Herein an blue light induced LiBr-promoted carbene insertion reaction of diazoesters into C(CO)—C bonds of 1,3-diones for the synthesis of a wide range of all-carbon quaternary center-containing 1,4-dione derivatives is reported. The method features good substrate universality and functional group compatibility, and therefore is an ideal and efficient strategy for the synthesis of 1,4-diones.

Key words: blue light, Lewis acid, carbene, 1, 3-dione, carbon-carbon bond cleavage

Cite this article

Dan Ba, Guolin Cheng. Blue Light Induced Insertion of Carbene into C(CO)—C Bonds of 1,3-Diones[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2888-2897.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

References 16

[1]	(a) Ertl, P.; Schuhmann, T. J. Nat. Prod. 2019, 82, 1258. doi: 10.1021/acs.jnatprod.8b01022
	(b) Walter, M. W. Nat. Prod. Rep. 2002, 19, 278. doi: 10.1039/b100919m
[2]	(a) Navale, B. S.; Laha, D.; Bhat, R. G. Tetrahedron Lett. 2019, 60, 1899. doi: 10.1016/j.tetlet.2019.06.026
	(b) Ren, Y.-Y.; Mao, H.-X.; Hu, M.-Y.; Zhu, S.-F.; Zhou, Q.-L. ChemCatChem 2020, 12, 4267. doi: 10.1002/cctc.202000684
	(c) Wu, Y.; He, X.; Xie, M.; Li, R.; Ning, Y.; Duan, J.; Zhang, E.; Shang, Y. J. Org. Chem. 2021, 86, 7370. doi: 10.1021/acs.joc.1c00259
	(d) Xi, Y.; Su, Y.; Yu, Z.; Dong, B.; McClain, E. J.; Lan, Y.; Shi, X. Angew. Chem., Int. Ed. 2014, 53, 9817. doi: 10.1002/anie.201404946
[3]	(a) Liu, Z.; Sivaguru, P.; Zanoni, G.; Anderson, E. A.; Bi, X. Angew. Chem., Int. Ed. 2018, 57, 8927. doi: 10.1002/anie.201802834
	(b) Liu, Z.; Zhang, X.; Virelli, M.; Zanoni, G.; Anderson, E. A.; Bi, X. iScience 2018, 8, 54. doi: 10.1016/j.isci.2018.09.006
	(c) Cao, S.; Liu, Z.; Yuan, H.; Yang, L.; Zhang, J.; Bi, X. Chin. J. Org. Chem. 2020, 40, 2468. (in Chinese)
	(曹姗姗, 刘兆洪, 袁海艳, 杨柳, 张景萍, 毕锡和, 有机化学, 2020, 40, 2468.) doi: 10.6023/cjoc202003003
	(d) Ning, Y.; Song, Q.; Sivaguru, P.; Wu, L.; Anderson, E. A.; Bi, X. Org. Lett. 2022, 24, 631. doi: 10.1021/acs.orglett.1c04081
[4]	Luo, K.; Mao, S.; He, K.; Yu, X.; Pan, J.; Lin, J.; Shao, Z.; Jin, Y. ACS Catal. 2020, 10, 3733. doi: 10.1021/acscatal.9b05360
[5]	Ba, D.; Wen, S.; Tian, Q.; Chen, Y.; Lv, W.; Cheng, G. Nat. Commun. 2020, 11, 4219. doi: 10.1038/s41467-020-17990-z
[6]	Wen, S.; Lv, W.; Ba, D.; Liu, J.; Cheng, G. Chem. Sci. 2019, 10, 9104. doi: 10.1039/c9sc03245b pmid: 31827753
[7]	(a) Yang, Z.; Stivanin, M. L.; Jurberg, I. D.; Koenigs, R.M. Chem. Soc. Rev. 2020, 49, 6833. doi: 10.1039/D0CS00224K pmid: 30543264
	(b) Ciszewski, Ł. W.; Rybicka-Jasińska, K.; Gryko, D. Org. Biomol. Chem. 2019, 17, 432. doi: 10.1039/c8ob02703j pmid: 30543264
[8]	(a) Empel, C.; Patureau, F. W.; Koenigs, R. M. J. Org. Chem. 2019, 84, 11316. doi: 10.1021/acs.joc.9b01753
	(b) Okada, C. Y.; dos Santos, C. Y.; Jurberg, I. D. Tetrahedron 2020, 76, 131316. doi: 10.1016/j.tet.2020.131316
	(c) Empel, C.; Jana, S.; Pei, C.; Nguyen, T. V.; Koenigs, R. M. Org. Lett. 2020, 22, 7225. doi: 10.1021/acs.orglett.0c02564
	(d) Qi, Z.; Wang, S. Org. Lett. 2021, 23, 8549. doi: 10.1021/acs.orglett.1c03252
	(e) Qin, L.-Z.; Yuan, X.; Cui, Y.-S.; Sun, Q.; Duan, X.; Zhuang, K.-Q.; Chen, L.; Qiu, J.-K.; Guo, K. Adv. Synth. Catal. 2020, 362, 5093. doi: 10.1002/adsc.202000716
	(f) Yang, J.; Wang, G.; Chen, S.; Ma, B.; Zhou, H.; Song, M.; Liu, C.; Huo, C. Org. Biomol. Chem. 2020, 18, 9494. doi: 10.1039/D0OB02006K
	(g) He, F.; Li, F.; Koenigs, R. M. J. Org. Chem. 2020, 85, 1240. doi: 10.1021/acs.joc.9b02605
[9]	(a) Orłowska, K.; Rybicka-Jasińska, K.; Krajewski, P.; Gryko, D. Org. Lett. 2020, 22, 1018. doi: 10.1021/acs.orglett.9b04560
	(b) Jana, S.; Koenigs, R. M. Asian J. Org. Chem. 2019, 8, 683. doi: 10.1002/ajoc.201900099
	(c) Yang, J.; Wang, J.; Huang, H.; Qin, G.; Jiang, Y.; Xiao, T. Org. Lett. 2019, 21, 2654. doi: 10.1021/acs.orglett.9b00647
	(d) Yang, Z.; Guo, Y.; Koenigs, R. M. Chem.-Eur. J. 2019, 25, 6703. doi: 10.1002/chem.201900597
	(e) Jana, S.; Yang, Z.; Pei, C.; Xu, X.; Koenigs, R. M. Chem. Sci. 2019, 10, 10129. doi: 10.1039/C9SC04069B
[10]	(a) He, F.; Koenigs, R. M. Chem. Commun. 2019, 55, 4881. doi: 10.1039/C9CC00927B pmid: 30480350
	(b) Guo, Y.; Nguyen, T. V.; Koenigs, R. M. Org. Lett. 2019, 21, 8814. doi: 10.1021/acs.orglett.9b03453 pmid: 30480350
	(c) Jurberg, I. D.; Davies, H. M. L. Chem. Sci. 2018, 9, 5112. doi: 10.1039/c8sc01165f pmid: 30480350
	(d) Hommelsheim, R.; Guo, Y.; Yang, Z.; Empel, C.; Koenigs, R. M. Angew. Chem., Int. Ed. 2019, 58, 1203. doi: 10.1002/anie.201811991 pmid: 30480350
	(e) Ye, C.; Cai, B.-G.; Lu, J.; Cheng, X.; Li, L.; Pan, Z.-W.; Xuan, J. J. Org. Chem. 2021, 86, 1012. doi: 10.1021/acs.joc.0c02500 pmid: 30480350
	(f) Xiao, T.; Mei, M.; He, Y.; Zhou, L. Chem. Commun. 2018, 54, 8865. doi: 10.1039/C8CC04609C pmid: 30480350
[11]	(a) Ye, C.; Cai, B.-G.; Lu, J.; Cheng, X.; Li, L.; Pan, Z.-W.; Xuan, J. J. Org. Chem. 2021, 86, 1012. doi: 10.1021/acs.joc.0c02500
	(b) Xiao, T.; Mei, M.; He, Y.; Zhou, L. Chem. Commun. 2018, 54, 8865. doi: 10.1039/C8CC04609C
[12]	Wen, S.; Tian, Q.; Chen, Y.; Zhang, Y.; Cheng, G. Org. Lett. 2021, 23, 7407. doi: 10.1021/acs.orglett.1c02598
[13]	Gallo, R. D. C.; Duarte, M.; da Silva, A. F.; Okada, C. Y.; Deflon, V. M.; Jurberg, I. D. Org. Lett. 2021, 23, 8916. doi: 10.1021/acs.orglett.1c03406
[14]	Keipour, H.; Ollevier, T. Org. Lett. 2017, 19, 5736. doi: 10.1021/acs.orglett.7b02488 pmid: 29028345
[15]	Howard, J.-L.; Sagatov, Y.; Repusseau, L.; Schotten, C.; Browne, D.-L. Green Chem. 2017, 19, 2798. doi: 10.1039/C6GC03139K
[16]	(a) Peng, S.; Lin, Y.-W.; He, W.-M. Chin. J. Org. Chem. 2020, 40, 541. (in Chinese) doi: 10.6023/cjoc202000006
	(彭莎, 林英武, 何卫民, 有机化学, 2020, 40, 541.) doi: 10.6023/cjoc202000006
	(b) Wang, Z.; Liu, Q.; Ji, X.; Deng, G.-J.; Huang, H. ACS Catal. 2020, 10, 154. doi: 10.1021/acscatal.9b04411
	(c) Ji, X.; Liu, Q.; Wang, Z.; Wang, P.; Deng, G.-J.; Huang, H. Green Chem. 2020, 22, 8233. doi: 10.1039/D0GC01872D

Entry	Additive	Solvent	Light source	Yield^b/%
1	—	DCM	Blue LEDs	45
2	—	DCE	Blue LEDs	33
3	—	CHCl₃	Blue LEDs	37
4	—	DMSO	Blue LEDs	0
5	—	MeCN	Blue LEDs	23
6	—	EA	Blue LEDs	30
7	—	Toluene	Blue LEDs	41
8	—	THF	Blue LEDs	0
9	—	MeOH	Blue LEDs	Trace
10	—	DMF	Blue LEDs	0
11	Pyridine	DCM	Blue LEDs	Trace
12	DBU	DCM	Blue LEDs	34
13	Et₃N	DCM	Blue LEDs	35
14	CsF	DCM	Blue LEDs	Trace
15	^tBuONa	DCM	Blue LEDs	Trace
16	Na₂CO₃	DCM	Blue LEDs	38
17	KI	DCM	Blue LEDs	47
18	K₂CO₃	DCM	Blue LEDs	26
19	KBr	DCM	Blue LEDs	49
20	LiBr	DCM	Blue LEDs	51
21	LiOH	DCM	Blue LEDs	Trace
22	LiCl	DCM	Blue LEDs	43
23	LiF	DCM	Blue LEDs	46
24	LiBr	DCM	Green LEDs	0
25	LiBr	DCM	Orange LEDs	0
26	LiBr	DCM	UV LEDs	Trace
27	LiBr	DCM	White LEDs	40
28	LiBr	DCM	Dark	0
29^c	LiBr	DCM	Blue LEDs	51
30^d	LiBr	DCM	Blue LEDs	49
31^e	LiBr	DCM	Blue LEDs	75
32^f	LiBr	DCM	Blue LEDs	60
33^g	LiBr	DCM	Blue LEDs	83
34^h	LiBr	DCM	Blue LEDs	81

Entry	Additive	Solvent	Light source	Yield^b/%
1	—	DCM	Blue LEDs	45
2	—	DCE	Blue LEDs	33
3	—	CHCl₃	Blue LEDs	37
4	—	DMSO	Blue LEDs	0
5	—	MeCN	Blue LEDs	23
6	—	EA	Blue LEDs	30
7	—	Toluene	Blue LEDs	41
8	—	THF	Blue LEDs	0
9	—	MeOH	Blue LEDs	Trace
10	—	DMF	Blue LEDs	0
11	Pyridine	DCM	Blue LEDs	Trace
12	DBU	DCM	Blue LEDs	34
13	Et₃N	DCM	Blue LEDs	35
14	CsF	DCM	Blue LEDs	Trace
15	^tBuONa	DCM	Blue LEDs	Trace
16	Na₂CO₃	DCM	Blue LEDs	38
17	KI	DCM	Blue LEDs	47
18	K₂CO₃	DCM	Blue LEDs	26
19	KBr	DCM	Blue LEDs	49
20	LiBr	DCM	Blue LEDs	51
21	LiOH	DCM	Blue LEDs	Trace
22	LiCl	DCM	Blue LEDs	43
23	LiF	DCM	Blue LEDs	46
24	LiBr	DCM	Green LEDs	0
25	LiBr	DCM	Orange LEDs	0
26	LiBr	DCM	UV LEDs	Trace
27	LiBr	DCM	White LEDs	40
28	LiBr	DCM	Dark	0
29^c	LiBr	DCM	Blue LEDs	51
30^d	LiBr	DCM	Blue LEDs	49
31^e	LiBr	DCM	Blue LEDs	75
32^f	LiBr	DCM	Blue LEDs	60
33^g	LiBr	DCM	Blue LEDs	83
34^h	LiBr	DCM	Blue LEDs	81

蓝光诱导的1,3-二酮C(CO)—C键卡宾插入反应