1,4-二氮杂二环[2.2.2]辛烷促进三酮单水合物和活泼炔通过连续碳-碳/碳-氧键断裂的加成反应

doi:10.6023/cjoc202104016

有机化学 ›› 2021, Vol. 41 ›› Issue (11): 4384-4390.DOI: 10.6023/cjoc202104016 上一篇下一篇

研究论文

1,4-二氮杂二环[2.2.2]辛烷促进三酮单水合物和活泼炔通过连续碳-碳/碳-氧键断裂的加成反应

张金凤, 叶如意, 李子阳, 孟令国^*()

淮北师范大学化学与材料科学学院安徽淮北 235000

收稿日期:2021-04-08 修回日期:2021-06-01 发布日期:2021-08-17
通讯作者: 孟令国
基金资助:
安徽高校自然科学研究基金(KJ2020A0045); 安徽高校自然科学研究基金(KJ2020B01)

1,4-Diazabicyclo[2.2.2]octane-Promoted Addition Reaction of Tricarbonyl Monohydrates with Active Alkynes via Consecutive C—C/C—O Cleavage

Jinfeng Zhang, Ruyi Ye, Ziyang Li, Lingguo Meng()

School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000

Received:2021-04-08 Revised:2021-06-01 Published:2021-08-17
Contact: Lingguo Meng
Supported by:
Natural Science Foundation of Educational Committee of Anhui Province(KJ2020A0045); Natural Science Foundation of Educational Committee of Anhui Province(KJ2020B01)

文章分享

1. 0253-2786-41-11-4384辅助材料.pdf(4809KB)

摘要/Abstract

在无金属和温和反应条件下, 发展了新颖的三酮单水合物与活泼炔通过连续碳-碳/碳-氧断裂的加成反应, 且反应可高效地在1 min内完成. 多样的三酮单水合物均可在1,4-二氮杂二环[2.2.2]辛烷(DABCO)的促进下, 通过这种转变与活泼炔反应, 生成多种酯类化合物.

关键词: 碳-碳键断裂, 碳-氧键断裂, 加成, 促进

A novel addition reaction of vicinal tricarbonyl monohydrates with active alkynes proceeded via rapid consecutive C—C/C—O cleavage processes under metal-free and mild reaction conditions, and the transformation was completed within only 1 min. Diverse tricarbonyl monohydrates could react with active alkynes to produce carboxylate esters via these transformations in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO).

Key words: C—C cleavage, C—O cleavage, addition, promoter

引用此文

张金凤, 叶如意, 李子阳, 孟令国. 1,4-二氮杂二环[2.2.2]辛烷促进三酮单水合物和活泼炔通过连续碳-碳/碳-氧键断裂的加成反应[J]. 有机化学, 2021, 41(11): 4384-4390.

Jinfeng Zhang, Ruyi Ye, Ziyang Li, Lingguo Meng. 1,4-Diazabicyclo[2.2.2]octane-Promoted Addition Reaction of Tricarbonyl Monohydrates with Active Alkynes via Consecutive C—C/C—O Cleavage[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4384-4390.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 6

参考文献 19

[1]	Fuji, K. Bond-Cleavage Reactions with Hard Acid and Soft Nucleophile Systems, Advances in Chemistry, ACS Symposium Series, American Chemical Society, Washington, DC, 1987, Vol. 215, p. 219.
[2]	For selected reviews, see: (a) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759. doi: 10.1021/cr960118r
	(b) Tobisu, M.; Chatani, N. Chem. Soc. Rev. 2008, 37, 300. doi: 10.1039/B702940N
[3]	For selected reviews, see: (a) Lu, H.; Yu, T.-Y.; Xu, P.-F.; Wei, H. Chem. Rev. 2021, 121, 365. doi: 10.1021/acs.chemrev.0c00153 pmid: 33085458
	(b) Lutz, M. D. R.; Morandi, B. Chem. Rev. 2021, 121, 300. doi: 10.1021/acs.chemrev.0c00154 pmid: 33085458
	(c) McDonald, T. R.; Mills, R. M.; West, M. S.; Rousseaux, S. A. L. Chem. Rev. 2021, 121, 3. doi: 10.1021/acs.chemrev.0c00346 pmid: 33085458
	(d) Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610. doi: 10.1039/B308864M pmid: 33085458
	(e) Wu, J.; Zhu, J.; Li, H.; Wu, C.; Shen, R.; Yu, L. Chin. J. Org. Chem. 2019, 39, 573. (in Chinese) doi: 10.6023/cjoc201809004 pmid: 33085458
	(吴锦雯, 朱佳雯, 李慧, 吴春雷, 沈润溥, 余乐茂, 有机化学, 2019, 39, 573.) pmid: 33085458
[4]	For selected examples, see: (a) Suginome, M..; Matsuda, T.; Ito,, Y. J. Am. Chem. Soc. 2000, 122, 11015. doi: 10.1021/ja002885k pmid: 22721172
	(b) Youn, S. W.; Kim, B. S.; Jagdale, A. R. J. Am. Chem. Soc. 2012, 134, 11308. doi: 10.1021/ja304616q pmid: 22721172
	(c) Zhou, M.-B.; Luo, M.-J.; Hu, M.; Li, J.-H. Chin. J. Chem. 2020, 38, 553. doi: 10.1002/cjoc.v38.6 pmid: 22721172
[5]	For selected examples, see: (a) Onodera, S.; Ishikawa, S.; Kochi, T.; Fakiuchi, F. J. Am. Chem. Soc. 2018, 140, 9788. doi: 10.1021/jacs.8b03718 pmid: 17994743
	(b) Chatani, N.; Le, Y.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1999, 121, 8645. doi: 10.1021/ja992048m pmid: 17994743
	(c) Cheng, C.-W.; Kuo, Y.-C.; Chang, S.-H.; Lin, Y.-C.; Liu, Y.-H.; Wang, Y. J. Am. Chem. Soc. 2007, 129, 14974. pmid: 17994743
[6]	For selected examples, see: (a) Brendel, M.; Sakhare, P. R.; Dahiya, G.; Subramanian, P.; Kaliappan, K. P. J. Org. Chem. 2020, 85, 8102. doi: 10.1021/acs.joc.0c00982 pmid: 23998269
	(b) Fan, W.; Yang, Y.; Lei, J.; Jiang, Q.; Zhou, W. J. Org. Chem. 2015, 80, 8782. doi: 10.1021/acs.joc.5b01670 pmid: 23998269
	(c) Zhu, Y.; Yan, H.; Lu, L.; Liu, D.; Rong, G.; Mao, J. J. Org. Chem. 2013, 78, 9898. doi: 10.1021/jo4016387 pmid: 23998269
	(d) Zhang, L.; Bi, X.; Guan, X.; Li, X.; Liu, Q. Angew. Chem., nt. Ed. 2013, 52, 11303. pmid: 23998269
[7]	For selected examples, see: (a) Wang, T.; Jiao, N. J. Am. Chem. Soc. 2013, 135, 11692. doi: 10.1021/ja403824y
	(b) Liang, D.; He, Y.; Liu, L.; Zhu, Q. Org. Lett. 2013, 15, 3476. doi: 10.1021/ol4015656
[8]	For selected examples, see: (a) Ji, T.; Chen, X.-Y.; Huang, L.; Rueping, M. Org. Lett. 2020, 22, 2579. doi: 10.1021/acs.orglett.0c00493
	(b) Zhu, S.; Das, A.; Bui, L.; Zhou, H.; Curran, D. P.; Rueping, M. J. Am. Chem. Soc. 2013, 135, 1823. doi: 10.1021/ja309580a
	(c) Zou, S.; Li, R.; Kobayashi, H.; Liu, J.; Fan, J. Chem. Commun. 2013, 49, 1906. doi: 10.1039/c2cc37277k
	(d) Song, C.; Shen, X.; Yu, F.; He, Y.; Yu, S. Chin. J. Org. Chem. 2020, 40, 3748. (in Chinese) doi: 10.6023/cjoc202004008
	(宋常华, 沈许, 于芳, 何宇鹏, 俞寿云, 有机化学, 2020, 40, 3748.) doi: 10.6023/cjoc202004008
	(e) Zhao, B.; Tan, H.; Chen, C.; Jiao, N.; Shi, Z. Chin. J. Chem. 2018, 36, 995. doi: 10.1002/cjoc.201800206
[9]	(a) Mecinovic, J.; Hamed, R. B.; Schofield, C. J. Angew. Chem., nt. Ed. 2009, 48, 2796. pmid: 23214721
	(b) Allpress, C. J.; Grubel, K.; Szajna-Fuller, E.; Arif, A. M.; Berreau, L. M. J. Am. Chem. Soc. 2013, 135, 659. doi: 10.1021/ja3038189 pmid: 23214721
[10]	Kohler, E.; Erickson, J. L. E. J. Am. Chem. Soc. 1931, 53, 2301. doi: 10.1021/ja01357a039
[11]	Barany, H. C.; Pianka, M.; Waters, W. A.; Schönberg, A.; Mou- basher, R.; Mostafa, A. J. Chem. Soc. 1946, 965.
[12]	Schönberg, A.; Azzam, R. C. J. Chem. Soc. 1939, 1428.
[13]	Tada, N.; Shomura, M.; Cui, L.; Nobuta, T.; Miura, T.; Itoh, A. Synlett 2011, 2896.
[14]	Berreau, L. M.; Grubel, K.; Allpress, C. J.; Borowski, T.; Wikstrom, J. P.; Germain, M. E.; Rybak-Akimova, E. V.; Tierney, D. L. Inorg. Chem. 2011, 50, 1047. doi: 10.1021/ic1017888 pmid: 21222442
[15]	Schönberg, A.; Mustafa, A. J. Chem. Soc. 1947, 997.
[16]	For selected recent reviews see: (a) Guo, H.; Fan, Y.; Sun, Z.; Wu, Y.; Kwon, O. Chem. Rev. 2018, 118, 10049. doi: 10.1021/acs.chemrev.8b00081
	(b) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535. doi: 10.1021/ar000253x
	(c) Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140. doi: 10.1039/b717758e
[17]	(a) Nair, V.; Pillai, A. N.; Menon, R. S.; Suresh, E. Org. Lett. 2005, 7, 1189. doi: 10.1021/ol050225k
	(b) Guo, H.; Xu, Q.; Kwon, O. J. Am. Chem. Soc. 2009, 131, 6318. doi: 10.1021/ja8097349
	(c) Wu, J.-Y.; Luo, Z.-B.; Dai, L.-X.; Hou, X.-L. J. Org. Chem. 2008, 73, 9137. doi: 10.1021/jo801703h
	(d) Garima.; Srivastava, V. P.; Yadav, L. D. S. Green Chem. 2010, 12, 1460. doi: 10.1039/c004736h
	(e) Meng, L.-G.; Hu, B.; Wu, Q.-P.; Liang, M.; Xue, S. Chem. Commun. 2009, 6089.
[18]	(a) Meng, L.-G.; Wang, L. Chem. Commun. 2012, 48, 3242. doi: 10.1039/c2cc30317e
	(b) Meng, L.-G.; Wang, L. Adv. Synth. Catal. 2013, 355, 2967. doi: 10.1002/adsc.v355.14/15
	(c) Meng, L.-G.; Ge, N.-L.; Yang, M.-M.; Wang, L. Eur. J. Org. Chem. 2011, 3403.
[19]	(a) Stang, P. J. Acc. Chem. Res. 1991, 24, 304. doi: 10.1021/ar00010a004 pmid: 21391562
	(b) Ackermann, L. Chem. Rev. 2011, 111, 1315. doi: 10.1021/cr100412j pmid: 21391562

Entry	Solvent	Base	Yield^b
1	CH₂Cl₂	DABCO	25^c
2	CH₂Cl₂	DABCO	36^d
3	CH₂Cl₂	DABCO	45
4	CH₂Cl₂	DABCO	18^e
5	CH₂Cl₂	DABCO	<10^f
6	CH₂Cl₂	DABCO	Complex^g
7	CH₂Cl₂	Et₃N	13
8	CH₂Cl₂	Pyridine	Trace
9	CH₂Cl₂	DBU	Trace
10	CH₂Cl₂	DMAP	ND^h
11	CH₂Cl₂	HMTA	NRⁱ
12	CH₂Cl₂	PPh₃	ND^h
13	CH₂Cl₂	K₂CO₃	NRⁱ
14	CH₂Cl₂	KOBu^t	NRⁱ
15	CHCl₃	DABCO	17
16	THF	DABCO	12
17	CCl₄	DABCO	Trace
18	CH₃CN	DABCO	Trace
19	CS₂	DABCO	Trace
20	Toluene	DABCO	Trace
21	EtOAc	DABCO	Trace
22	DMF	DABCO	ND^h

Entry	Solvent	Base	Yield^b
1	CH₂Cl₂	DABCO	25^c
2	CH₂Cl₂	DABCO	36^d
3	CH₂Cl₂	DABCO	45
4	CH₂Cl₂	DABCO	18^e
5	CH₂Cl₂	DABCO	<10^f
6	CH₂Cl₂	DABCO	Complex^g
7	CH₂Cl₂	Et₃N	13
8	CH₂Cl₂	Pyridine	Trace
9	CH₂Cl₂	DBU	Trace
10	CH₂Cl₂	DMAP	ND^h
11	CH₂Cl₂	HMTA	NRⁱ
12	CH₂Cl₂	PPh₃	ND^h
13	CH₂Cl₂	K₂CO₃	NRⁱ
14	CH₂Cl₂	KOBu^t	NRⁱ
15	CHCl₃	DABCO	17
16	THF	DABCO	12
17	CCl₄	DABCO	Trace
18	CH₃CN	DABCO	Trace
19	CS₂	DABCO	Trace
20	Toluene	DABCO	Trace
21	EtOAc	DABCO	Trace
22	DMF	DABCO	ND^h

1,4-二氮杂二环[2.2.2]辛烷促进三酮单水合物和活泼炔通过连续碳-碳/碳-氧键断裂的加成反应

1,4-Diazabicyclo[2.2.2]octane-Promoted Addition Reaction of Tricarbonyl Monohydrates with Active Alkynes via Consecutive C—C/C—O Cleavage

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 6

参考文献 19

相关文章 15

编辑推荐

相关统计

本文评价

[1]	童红恩, 郭宏宇, 周荣. 可见光促进惰性碳-氢键对羰基的加成反应进展[J]. 有机化学, 2024, 44(1): 54-69.
[2]	李梦竹, 孟博莹, 兰文捷, 傅滨. 邻亚甲醌与硫叶立德反应合成2,3-二取代苯并二氢呋喃化合物[J]. 有机化学, 2024, 44(1): 195-203.
[3]	王化坤, 任晓龙, 宣宜宁. 卤盐催化的α,β-环氧羧酸酯与异氰酸酯[3＋2]环加成反应研究[J]. 有机化学, 2024, 44(1): 251-258.
[4]	孟宪强, 杨艺, 梁万洁, 王靖涛, 张荣葵, 刘会. 钯催化联烯胺区域选择性芳基酚氧化反应[J]. 有机化学, 2024, 44(1): 224-231.
[5]	马虎, 黄丹凤, 王克虎, 唐朵朵, 冯杨, 任园园, 王君娇, 胡雨来. 3-(三氟甲基)吡唑类化合物的合成[J]. 有机化学, 2023, 43(9): 3257-3267.
[6]	张俊杰, 徐学涛. (S)-(–)-Xylopinine和(S)-(+)-Laudanosine的不对称合成[J]. 有机化学, 2023, 43(9): 3297-3303.
[7]	陈祖佳, 宇世伟, 周永军, 李焕清, 邱琪雯, 李妙欣, 汪朝阳. BF₃•OEt₂作为催化剂与合成子在有机合成中的应用进展[J]. 有机化学, 2023, 43(9): 3107-3118.
[8]	张建涛, 张聪, 莫诺琳, 罗佳婷, 陈莲芬, 刘卫兵. 氯仿参与的烯烃自由基加成反应的研究进展[J]. 有机化学, 2023, 43(9): 3098-3106.
[9]	陈祖良, 魏颖静, 张俊良. 供体-受体氮杂环丙烷碳-碳键断裂的环加成反应研究进展[J]. 有机化学, 2023, 43(9): 3078-3088.
[10]	王熠, 张键, 刘飏子, 罗晓燕, 邓卫平. 钯催化不对称[3＋4]环加成构建吲哚并环庚烷[J]. 有机化学, 2023, 43(8): 2864-2877.
[11]	雷容超, 兰文捷, 李梦竹, 傅滨. 苯并磺内酰胺联吡唑化合物的简便合成[J]. 有机化学, 2023, 43(7): 2553-2560.
[12]	周林, 杨鸿, 杨川, 赵志刚, 李清寒. 非共轭丁烯内酯α-和β-位反应研究进展[J]. 有机化学, 2023, 43(7): 2407-2424.
[13]	马佳敏, 李姣兄, 孟千森, 曾祥华. 炔烃的自由基砜基化反应研究进展[J]. 有机化学, 2023, 43(6): 2040-2052.
[14]	吕敏, 杨爱梅, 张昱, 孙建婷, 魏邦国. Fe(OTf)₃催化含有N,O-缩醛结构硼酸酯的合成研究[J]. 有机化学, 2023, 43(5): 1777-1785.
[15]	孔德亮, 戴闻, 赵怡玲, 陈艺林, 朱红平. 脒基胺硼基硅宾与单酮和二酮的氧化环加成反应研究[J]. 有机化学, 2023, 43(5): 1843-1851.