Copper Corrole as an Efficient Catalyst for Esterification of Allylic sp3-C—H Bonds with Carboxylic Acids

doi:10.6023/cjoc202101023

Abstract

Copper 5,10,15-tris(pentafluorophenyl)corrole (CuTPFC) catalyzed oxidative cross dehydrogenative coupling (CDC) of allylic sp³-C—H bonds and acids had been investigated in a homogeneous system, which provided allylic esters smoothly. This reaction proceeded with broad substrate scope and good functional group tolerance. In a gram scale test, the turnover number (TON) reached 5100 at only 0.01 mol% catalyst loading, indicating the current catalytic system has potential uses in the allylic esters.

Key words: copper, corrole, cross dehydrogenative coupling, allylic compounds, catalysis

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Wanqun Tian, Mengyuan Li, Shuang Yang, Hao Zhang, Haiyang Liu, Xinyan Xiao. Copper Corrole as an Efficient Catalyst for Esterification of Allylic sp³-C—H Bonds with Carboxylic Acids[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2875-2884.

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References 31

[1]	(a) Saito, T.; Fuwa, H.; Sasaki, M. Org. Lett. 2009, 11,5274. doi: 10.1021/ol902217q
	(b) Kolodziej, H.; Burmeister, A.; Trun, W.; Radtke,O. A.; Kiderlen,A. F.; Ito, H.; Hatano, T.; Yoshida, T.; Foo,L. Y. Bioorg. Med. Chem. 2005, 13,6470. doi: 10.1016/j.bmc.2005.07.012
	(c) Takeuchi, Y.; Shi,Q. W.; Sugiyama, T.; Oritani, T. Biosci. Biotechnol. Biochem. 2002, 66,537. doi: 10.1271/bbb.66.537
	(d) Kijjoa, A.; Bessa, J.; Pinto,M. M.; Anatachoke, C.; Silva,A. M.; Eaton, G.; Herz, W. Phytochemistry 2002, 59,543. doi: 10.1016/S0031-9422(01)00465-4
	(e) Covell,D. J.; Vermeulen,N. A.; Labenz,N. A.; White,M. C. Angew. Chem.,Int. Ed. 2006, 45,8217. doi: 10.1002/(ISSN)1521-3773
	(f) Huong,D. T.; Kamperdick, C.; Sung,T. V. J. Nat. Prod. 2004, 67,445. doi: 10.1021/np030195z
[2]	(a) Kharasch,M. S.; Sosnovsky, G.; Yang,N. C. J. Am. Chem. Soc. 1959, 81,5819. doi: 10.1021/ja01530a067
	(b) Kharasch,M. S.; Sosnovsky, G. J. Am. Chem. Soc. 1958, 80,756.
[3]	(a) Shi,E. B.; Shao, Y.; Chen,S. L.; Hu,H. Y.; Liu,Z. J.; Zhang, J.; Wan,X. B. Org. Lett. 2012, 14,3384. doi: 10.1021/ol3013606
	(b) Aakermark, B.; Larsson,E. M.; Oslob,J. D. J. Org. Chem. 1994, 59,5729. doi: 10.1021/jo00098a035
[4]	(a) Ashenhurst,J. A. Chem. Soc. Rev. 2010, 39,540. doi: 10.1039/B907809F
	(b) Scheuermann,C. J. Chem.-Asian J. 2010, 5,436. doi: 10.1002/asia.v5:3
	(c) Lv, L.; Li, Z. Top. Curr. Chem. 2016, 374,38.
	(d) Li,C. J. Acc. Chem. Res. 2009, 42,335. doi: 10.1021/ar800164n
	(e) Girard,S. A.; Knauber, T.; Li,C. J. Angew. Chem.,Int. Ed. 2014, 53,74.
	(f) Faisca Phillips, A.M.; Pombeiro, A.J.L. ChemCatChem 2018, 10,3354. doi: 10.1002/cctc.201800582
[5]	(a) Young,A. J.; White,M. C. J. Am. Chem. Soc. 2008, 130,14090. doi: 10.1021/ja806867p
	(b) Su, X.; Surry,D. S.; Spandl,R. J.; Spring,D. R. Org. Lett. 2008, 10,2593. doi: 10.1021/ol8009545
	(c) Meng, Z.; Sun, S.; Yuan, H.; Lou, H.; Liu, L. Angew. Chem.,Int. Ed. 2014, 53,543. doi: 10.1002/anie.v53.2
	(d) Liu,Z. Q.; Zhao, L.; Shang, X.; Cui, Z. Org. Lett. 2012, 14,3218. doi: 10.1021/ol301220s
	(e) Lin, S.; Song,C. X.; Cai,G. X.; Wang,W. H.; Shi,Z. J. J. Am. Chem. Soc. 2008, 130,12901. doi: 10.1021/ja803452p
	(f) Li, Z.; Bohle,D. S.; Li,C. J. Proc. Natl. Acad. Sci. U. S. A. 2006, 103,8928. doi: 10.1073/pnas.0601687103
	(g) Zhao, S.; Yuan, J.; Li,Y. C.; Shi,B. F. Chem. Commun. 2015, 51,12823. doi: 10.1039/C5CC05058H
	(h) Zhao, J.; Fang, H.; Zhou, W.; Han, J.; Pan, Y. J. Org. Chem. 2014, 79,3847. doi: 10.1021/jo500192h
	(i) Tsang,A. S.; Kapat, A.; Schoenebeck, F. J. Am. Chem. Soc. 2016, 138,518. doi: 10.1021/jacs.5b08347
	(j) Sun, S.; Li, C.; Floreancig,P. E.; Lou, H.; Liu, L. Org. Lett. 2015, 17,1684. doi: 10.1021/acs.orglett.5b00447
	(k) Liang,Y. F.; Jiao, N. Angew. Chem.,Int. Ed. 2014, 53,548. doi: 10.1002/anie.v53.2
	(l) Pan, X.; Liu, X.; Sun, S.; Meng, Z.; Liu, L. Chin. J. Chem. 2018, 36,1187. doi: 10.1002/cjoc.v36.12
	(m) Lu, F.; Yang, Z.; Wang, T.; Wang, T.; Zhang, Y.; Yuan, Y.; Lei, A. Chin. J. Chem. 2019, 37,547. doi: 10.1002/cjoc.v37.6
	(n) Xiao,Y. X.; Liu,Z. Q. Acta Chim. Sinica 2019, 77,874 (in Chinese). doi: 10.6023/A19050189
	( 肖莹霞, 柳忠全, 化学学报, 2019, 77,874.)
[6]	Shi, E.; Shao, Y.; Chen, S.; Hu, H.; Liu, Z.; Zhang, J.; Wan, X. Org. Lett. 2012, 14,3384. doi: 10.1021/ol3013606
[7]	Lu, B.; Zhu, F.; Wang, D.; Sun, H.; Shen, Q. Tetrahedron Lett. 2017, 58,2490. doi: 10.1016/j.tetlet.2017.05.039
[8]	Ren,T. -L.; Xu,B. -H.; Mahmood, S.; Sun,M. -X.; Zhang,S. -J. Tetrahedron 2017, 73,2943. doi: 10.1016/j.tet.2017.04.002
[9]	(a) Wang,C. Y.; Song,R. J.; Wei,W. T.; Fan,J. H.; Li,J. H. Chem. Commun. 2015, 51,2361. doi: 10.1039/C4CC09393C
	(b) Tran,B. L.; Driess, M.; Hartwig,J. F. J. Am. Chem. Soc. 2014, 136,17292. doi: 10.1021/ja510093x
	(c) Zhou, J.; Jin, C.; Li, X.; Su, W. RSC Adv. 2015, 5,7232. doi: 10.1039/C4RA14586K
[10]	Garcia-Cabeza,A. L.; Marin-Barrios, R.; Moreno-Dorado,F. J.; Ortega,M. J.; Massanet,G. M.; Guerra,F. M. Org. Lett. 2014, 16,1598. doi: 10.1021/ol500198c
[11]	(a) Ghosh, A. Chem. Rev. 2017, 117,3798. doi: 10.1021/acs.chemrev.6b00590
	(b) Barata,J. F.B.; Neves,M. G.P.M. S.; Faustino,M. A.F.; Tomé,A. C.; Cavaleiro,J. A.S. Chem. Rev. 2016, 117,3192. doi: 10.1021/acs.chemrev.6b00476
[12]	(a) Ali, A.; Akram, W.; Liu,H. Y. Molecules 2018, 24,78. doi: 10.3390/molecules24010078
	(b) Huang,L. -T.; Ali, A.; Wang,H. -H.; Cheng, F.; Liu,H. -Y. J. Mol. Catal. A: Chem. 2017, 426,213. doi: 10.1016/j.molcata.2016.11.019
[13]	(a) Chen,T. H.; Kwong,K. W.; Lee,N. F.; Ranburger, D.; Zhang, R. Inorg. Chim. Acta 2016, 451,65. doi: 10.1016/j.ica.2016.07.007
	(b) Ranburger, D.; Willis, B.; Kash, B.; Jeddi, H.; Alcantar, C.; Zhang, R. Inorg. Chim. Acta 2019, 487,41. doi: 10.1016/j.ica.2018.11.048
[14]	Sacramento,J. J.D.; Goldberg,D. P. Acc. Chem. Res. 2018, 51,2641. doi: 10.1021/acs.accounts.8b00414
[15]	(a) Li, P.; Cao, Z. Organometallics 2018, 37,406. doi: 10.1021/acs.organomet.7b00830
	(b) Tiffner, M.; Gonglach, S.; Haas, M.; Schofberger, W.; Waser, M. Chem. Asian J. 2017, 12,1048. doi: 10.1002/asia.201700354
[16]	Zhan, X.; Kolanu, S.; Fite, S.; Chen,Q. C.; Lee, W.; Churchill,D. G.; Gross, Z. Photochem. Photobiol. Sci. 2020, 19,996. doi: 10.1039/D0PP00218F
[17]	Nayak, M.; Nayak, P.; Sahu, K.; Kar, S. J. Org. Chem. 2020, 85,11654. doi: 10.1021/acs.joc.0c01146
[18]	Lai,J. -W.; Liu,Z. -Y.; Chen,X. -Y.; Zhang, H.; Liu,H. -Y. Tetrahedron Lett. 2020,61.
[19]	Schaffer, R.; Isbell,H. S. J. Am. Chem. Soc. 1958, 80,756.
[20]	Mayoral,J. A.; Rodriguez-Rodriguez, S.; Salvatella, L. Chem.-Eur. J. 2008, 14,9274. doi: 10.1002/chem.v14:30
[21]	Koszarna, B.; Gryko,D. T. J. Org. Chem. 2006, 71,3707. doi: 10.1021/jo060007k
[22]	(a) Luobeznova, I.; Simkhovich, L.; Goldberg, I.; Gross, Z. Eur. J. Inorg. Chem. 2004, 2004,1724.
	(b) Chen, Y.; Fan,Q. -H.; Hossain,M. S.; Zhan,S. -Z.; Liu,H. -Y.; Si,L. -P. Eur. J. Inorg. Chem. 2020, 2020,491. doi: 10.1002/ejic.201900996
[23]	Li, J.; Jia, X.; Deng, H.; Li, C.; Jin, T.; Li, C. Synlett 2018, 29,840. doi: 10.1055/s-0036-1591748
[24]	Liu, G.; Jin, C.; Wu, G. Synlett 2014, 25,2908. doi: 10.1055/s-00000083
[25]	Wright,B. J.; Hartung, J.; Peng, F.; Van de Water, R.; Liu, H.; Tan,Q. H.; Chou,T. C.; Danishefsky,S. J. J. Am. Chem. Soc. 2008, 130,16786. doi: 10.1021/ja805936v
[26]	Werkhoven,T. M.; Siebum,A. H.G.; Lugtenburg, J. Eur. J. Org. Chem. 2000, 2000,2113. doi: 10.1002/(ISSN)1099-0690
[27]	Tanaka, S.; Nakashima, T.; Satou, N.; Oono, H.; Kon, Y.; Tamura, M.; Sato, K. Tetrahedron Lett. 2019, 60,2009. doi: 10.1016/j.tetlet.2019.06.056
[28]	Sedighi, M.; Calimsiz, S.; Lipton,M. A. J. Org. Chem. 2006, 71,9517. doi: 10.1021/jo061207z
[29]	Mamone, P.; Grunberg,M. F.; Fromm, A.; Khan,B. A.; Goossen,L. J. Org. Lett. 2012, 14,3716. doi: 10.1021/ol301563g
[30]	Lim, S.; Ji, M.; Wang, X.; Lee, C.; Jang,H. -Y. Eur. J. Org. Chem. 2015, 2015,591. doi: 10.1002/ejoc.201403311
[31]	Whittaker,A. M.; Lalic, G. Org. Lett. 2013, 15,1112. doi: 10.1021/ol4001679

Entry	Catalyst (mol%)	Solvent	Oxidant	Yield^b/%	TON
1	CuTPFC (1.0)	Toluene	DTBP	47	47
2	CuTPFC (1.0)	CHCl₃	DTBP	36	36
3	CuTPFC (1.0)	MeOH	DTBP	20	20
4	CuTPFC (1.0)	CH₃CN	DTBP	Trace	—
5	CuTPFC (1.0)	THF	DTBP	N.D.^c	—
6	CuTPFC (1.0)	EA	DTBP	93	93
7	CuTPFC (1.0)	DCE	DTBP	95	95
8	CuTPFC (0.5)	DCE	DTBP	94	188
9	CuTPFC (0.1)	DCE	DTBP	97 (95^d)	970
10	CuTPFC (0.01)	DCE	DTBP	75	7500
11	CuTPFC (0.1)	DCE	TBHP	87	870
12	CuTPFC (0.1)	DCE	m-CPBA	15	150
13	CuTPFC (0.1)	DCE	H₂O₂	17	170
14	CuTPFC (0.1)	DCE	DDQ	N.D.^c	—
15	MnTPFC (0.1)	DCE	DTBP	9	90
16	CoTPFC (0.1)^e	DCE	DTBP	15	150
17	CuTPC (0.1)	DCE	DTBP	91	910
18	Cu(OAc)₂ (0.1)	DCE	DTBP	23	230
19	CuOAc (0.1)	DCE	DTBP	84	840
20	—	DCE	DTBP	10	—

Entry	Catalyst (mol%)	Solvent	Oxidant	Yield^b/%	TON
1	CuTPFC (1.0)	Toluene	DTBP	47	47
2	CuTPFC (1.0)	CHCl₃	DTBP	36	36
3	CuTPFC (1.0)	MeOH	DTBP	20	20
4	CuTPFC (1.0)	CH₃CN	DTBP	Trace	—
5	CuTPFC (1.0)	THF	DTBP	N.D.^c	—
6	CuTPFC (1.0)	EA	DTBP	93	93
7	CuTPFC (1.0)	DCE	DTBP	95	95
8	CuTPFC (0.5)	DCE	DTBP	94	188
9	CuTPFC (0.1)	DCE	DTBP	97 (95^d)	970
10	CuTPFC (0.01)	DCE	DTBP	75	7500
11	CuTPFC (0.1)	DCE	TBHP	87	870
12	CuTPFC (0.1)	DCE	m-CPBA	15	150
13	CuTPFC (0.1)	DCE	H₂O₂	17	170
14	CuTPFC (0.1)	DCE	DDQ	N.D.^c	—
15	MnTPFC (0.1)	DCE	DTBP	9	90
16	CoTPFC (0.1)^e	DCE	DTBP	15	150
17	CuTPC (0.1)	DCE	DTBP	91	910
18	Cu(OAc)₂ (0.1)	DCE	DTBP	23	230
19	CuOAc (0.1)	DCE	DTBP	84	840
20	—	DCE	DTBP	10	—

铜咔咯催化烯丙基sp³-C—H键与羧酸的酯化反应

Copper Corrole as an Efficient Catalyst for Esterification of Allylic sp³-C—H Bonds with Carboxylic Acids

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Entry	Catalyst	DTBP (equiv.)	Yield/%		Sum/%
Entry	Catalyst	DTBP (equiv.)	5a	3a	Sum/%
1	—	—	26	19	45
2	—	2	28	19	47
3	CuTPFC	—	10	42	52
4	CuTPFC	2	17	46	63
5	CuTPFC	4	16	49	65

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铜咔咯催化烯丙基sp3-C—H键与羧酸的酯化反应