Mechanochemistry Enabled Friedel-Crafts Alkylation Reactions of Donor-Acceptor Cyclopropanes with 2-Indolymethanols

doi:10.6023/cjoc202404006

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (11): 3437-3445.DOI: 10.6023/cjoc202404006 Previous Articles Next Articles

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机械力化学促进给-受体环丙烷与吲哚-2-二芳甲醇傅-克烷基化反应

梁金少, 阮丽红, 石栩溶, 陈樱枝, 宋楚焕, 肖军安, 刘志平^*()

南宁师范大学广西天然高分子化学与物理重点实验室南宁 530001

收稿日期:2024-04-06 修回日期:2024-05-20 发布日期:2024-06-13
基金资助:
国家自然科学基金(22261036); 广西自然科学基金(2020GXNSFAA159096)

Mechanochemistry Enabled Friedel-Crafts Alkylation Reactions of Donor-Acceptor Cyclopropanes with 2-Indolymethanols

Jinshao Liang, Lihong Ruan, Xurong Shi, Yinzhi Chen, Chuhuang Song, Jun'an Xiao, Zhiping Liu^*()

Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001

Received:2024-04-06 Revised:2024-05-20 Published:2024-06-13
Contact: *E-mail:liuzhiping828@126.com
Supported by:
National Natural Science Foundation of China(22261036); Guangxi Natural Science Foundation(2020GXNSFAA159096)

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Abstract

Mechanochemical synthesis of 3-substituted 2-indolymethanols through scandium(Ⅲ)/palladium(Ⅱ) synergistic catalyzed Friedel-Crafts alkylations of donor-acceptor cyclopropanes and 2-indolymethanols has been developed. A wide broad of 3-substituted 2-indolymethanols have been afforded in moderate to excellent yields. This strategy has the advantage of short reaction time, wide substrate scope, mild reaction conditions, and so on. The synthetic utility was further demonstrated by gram-scale reaction and derivatization of the desired product.

Key words: mechanochemistry, green chemistry, Friedel-Crafts alkylation, donor-acceptor cyclopropane

Cite this article

Jinshao Liang, Lihong Ruan, Xurong Shi, Yinzhi Chen, Chuhuang Song, Jun'an Xiao, Zhiping Liu. Mechanochemistry Enabled Friedel-Crafts Alkylation Reactions of Donor-Acceptor Cyclopropanes with 2-Indolymethanols[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3437-3445.

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References 15

[1]	(a) Do J.; Friscic T. ACS Cent. Sci. 2017, 3, 13. pmid: 36741531
	(b) Nicholson W. I.; Barreteau F.; Leitch J. A.; Payne R.; Priestley I.; Godineau E.; Battilocchio C.; Browne D. L. Angew. Chem., Int. Ed. 2021, 60, 21868. pmid: 36741531
	(c) Nicholson W. I.; Howard J. L.; Magri G.; Seastram A. C.; Khan A.; Bolt R. R. A.; Morrill L. C.; Richards E.; Browne D. L. Angew. Chem., Int. Ed. 2021, 60, 23312. pmid: 36741531
	(d) Reynes J. F.; Felipe G. Angew. Chem. 2023, 62, 1433. pmid: 36741531
	(e) Jones A. C.; Nicholson W. I.; Smallman H. R.; Browne D. L. Org. Lett. 2020, 22, 7433. pmid: 36741531
	(f) Jones A. C.; Nicholson W. I.; Leitch J. A.; Browne D. L. Org. Lett. 2021, 23, 6337. pmid: 36741531
	(g) Liu Y.; Li X.; Liu Q.; Li X.; Liu H. Org. Lett. 2022, 24, 6604. pmid: 36741531
	(h) Xu H.; Hong R.; Weng M. Y.; Huang R. L.; Wang G. W.; Zhang Z. Org. Lett. 2021, 23, 5305. pmid: 36741531
	(i) Takahashi R.; Gao P.; Kubota K.; Ito H. Chem. Sci. 2023, 14, 499. doi: 10.1039/d2sc05468j pmid: 36741531
	(j) Zhu S. E.; Li F.; Wang G. W. Chem. Soc. Rev. 2013, 42, 7535. pmid: 36741531
	(k) Wang G. W. Chem. Soc. Rev. 2013, 42, 7668. pmid: 36741531
[2]	(a) Cankařová N.; Schütznerová E.; Krchňák V. Chem. Rev. 2019, 119, 12089. doi: 10.1021/acs.chemrev.9b00465 pmid: 34351760
	(b) Porcheddu A.; Colacino E.; De Luca L.; Delogu F. ACS Catal. 2020, 10, 8344. pmid: 34351760
	(c) Takahashi R.; Seo T.; Kubota K.; Ito H. ACS Catal. 2021, 11, 14803. pmid: 34351760
	(d) Vadivelu M.; Sampath S.; Muthu K.; Karthikeyan K.; Praveen C. Adv. Synth. Catal. 2021, 363, 4941. pmid: 34351760
	(e) Zhang J.; Zhang P.; Ma Y.; Szostak M. Org. Lett. 2022, 24, 2338. pmid: 34351760
	(f) Wang Y.; Zhang Z.; Deng L.; Lao T.; Su Z.; Yu Y.; Cao H. Org. Lett. 2021, 23, 7171. pmid: 34351760
	(g) Gao Y.; Feng C.; Seo T.; Kubota K.; Ito H. Chem. Sci. 2022, 13, 430. pmid: 34351760
	(h) Chatterjee T.; Ranu B. C. J. Org. Chem. 2021, 86, 13895. doi: 10.1021/acs.joc.1c01454 pmid: 34351760
[3]	(a) Kandambeth S.; Dey K.; Banerjee R. J. Am. Chem. Soc. 2019, 141, 1807. doi: 10.1021/jacs.8b10334 pmid: 30485740
	(b) Schumacher C.; Hernández J. G.; Bolm C. Angew. Chem. 2020, 59, 16499. pmid: 30485740
	(c) Hao X.; Feng D.; Huang P.; Guo F. Org. Chem. Front. 2024, 11, 2081. pmid: 30485740
[4]	(a) Brahmachari G.; Karmakar I.; Karmakar P. Green Chem. 2021, 23, 4762.
	(b) Sharapov A. D.; Fatykhov R. F.; Khalymbadzha I. A.; Sharutin V. V.; Santra S.; Zyryanov G. V.; Chupakhin O. N.; Ranu B. C. Green Chem. 2022, 24, 2429.
	(c) Rodrigo E.; Wiechert R.; Walter M. W.; Braje W.; Geneste H. Green Chem. 2022, 24, 1469.
	(d) Kong D.; Bolm C. Green Chem. 2022, 24, 6476.
	(e) Xu Q.; Sheng X.; Li N.; Zhang J.; Shi H.; Niu M.; Ping Q.; Li N. ACS Sustainable Chem. Eng. 2021, 9, 8232.
	(f) Qin J.; Zuo H.; Ni Y.; Yu Q.; Zhong F. ACS Sustainable Chem. Eng. 2020, 8, 12342.
[5]	Zhang Y.; Jiang F.; Shi F. Acc. Chem. Res. 2020, 53, 425.
[6]	(a) Chen K.; Wang D.; Liu S.; Wang X.; Zhang Y.; Tian Y.; Wu Q.; Shi F. J. Org. Chem. 2021, 86, 10427.
	(b) Li T.; Liu S.; Sun Y.; Deng S.; Tan W.; Jiao Y.; Zhang Y.; Shi F. Angew. Chem., Int. Ed. 2021, 60, 2355.
[7]	Zhang H.; Shi F. Acc. Chem. Res. 2022, 55, 2562.
[8]	(a) Xu M.; Wang H.; Mao Y.; Mei G.; Wang S.; Shi F. J. Org. Chem. 2018, 83, 5027.
	(b) Hu C.; Hong G.; He Y.; Zhou C.; Kozlowski M. C.; Wang L. J. Org. Chem. 2018, 83, 4739.
	(c) Zhu Z.; Shen Y.; Liu J.; Tao J.; Shi F. Org. Lett. 2017, 19, 1542.
	(d) Ma C.; Zhou J.; Zhang Y.; Jiao Y.; Mei G.; Shi F. Chem. Asian J. 2018, 13, 2549.
[9]	(a) Xu M.; Wang H.; Wan Y.; Wang S.; Shi F. J. Org. Chem. 2017, 82, 10226.
	(b) Wang J.; Wu P.; Wu J.; Mei G.; Shi F. J. Org. Chem. 2018, 83, 5931.
	(c) Wu J.; Wang J.; Wu P.; Wang J.; Mei G.; Shi F. Org. Chem. Front. 2018, 5, 1436.
	(d) Shi Y. C.; Yan X. Y.; Wu P.; Jiang S.; Xu R.; Tan W.; Shi F. Chin. J. Chem. 2023, 41, 27.
	(e) Han T.; Wang M.; Mei G. Chem. Commun. 2021, 57, 8921.
[10]	(a) He Y.; Sun X.; Li G.; Mei G.; Shi F. J. Org. Chem. 2017, 82, 2462.
	(b) Zhu S.; Zhang Y.; Luo J.; Wang F.; Cao X.; Huang S. Green Chem. 2020, 22, 657.
[11]	Mei G.; Shi F. J. Org. Chem. 2017, 82, 7695.
[12]	Zhu Z.; Yu L.; Sun M.; Mei G.; Shi F. Adv. Synth. Catal. 2018, 360, 3109.
[13]	Deng S.; Qu C.; Jiao Y.; Liu W.; Shi F. J. Org. Chem. 2020, 85, 11641.
[14]	Mao J.; Zhang H.; Ding X.; Luo X.; Deng W. J. Org. Chem. 2019, 84, 11186.
[15]	Skvorcova M.; Grigorjeva L.; Jirgensons A. Org. Lett. 2015, 17, 2902. doi: 10.1021/acs.orglett.5b01014 pmid: 26039677

机械力化学促进给-受体环丙烷与吲哚-2-二芳甲醇傅-克烷基化反应

Mechanochemistry Enabled Friedel-Crafts Alkylation Reactions of Donor-Acceptor Cyclopropanes with 2-Indolymethanols

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Fig. & Tab. 6

References 15

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Entry	LA	LAG	t/min	Frequency/Hz	Yield^b/%
1	Cu(OTf)₂	—	60	35	26
2	Ni(OTf)₂	—	60	35	nd
3	Zn(OTf)₂	—	60	35	Trace
4	Bi(OTf)₂	—	60	35	Trace
5	Y(OTf)₃	—	60	35	17
6	Yb(OTf)₃	—	60	35	14
7	Sc(OTf)₃	—	60	35	35
8	Sc(OTf)₃	—	60	35	Trace^c
9	Sc(OTf)₃	Toluene	60	35	64
10	Sc(OTf)₃	CH₂Cl₂	60	35	83
11	Sc(OTf)₃	CH₂Cl₂	99	35	86
12	Sc(OTf)₃	CH₂Cl₂	40	35	81
13	Sc(OTf)₃	CH₂Cl₂	20	35	53
14	Sc(OTf)₃	CH₂Cl₂	99	25	76
15	Sc(OTf)₃	CH₂Cl₂	99	15	59

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