Nucleophilic Etherification of Heteroaryl Alkyl Ethers, Heteroaryl Halides with (Deuterated) Alcohols

doi:10.6023/cjoc202006077

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 795-805.DOI: 10.6023/cjoc202006077 Previous Articles Next Articles

Article

杂芳基烷基醚、杂芳基卤化物与(氘代)醇的亲核醚化

王霞¹, 屈益欣¹, 龙城宇¹, 王雪强¹^,^*()

1 湖南大学化学化工学院分子科学与生物医学实验室(MBL) 化学/生物传感与化学计量家重点实验室长沙 410082

收稿日期:2020-06-30 修回日期:2020-08-20 发布日期:2020-10-12
通讯作者: 王雪强
作者简介:
* Corresponding author. E-mail: wangxq@hnu.edu.cn
† 共同第一作者(These authors contributed equally to this work).
基金资助:
湖南省湖湘青年人才计划(2019RS2022)

Nucleophilic Etherification of Heteroaryl Alkyl Ethers, Heteroaryl Halides with (Deuterated) Alcohols

Xia Wang¹, Yixin Qu¹, Chengyu Long¹, Xue-Qiang Wang¹^,^*()

1 Molecular Science and Biomedicine Laboratory, State Key Laboratory of Chemo/Bio-sensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received:2020-06-30 Revised:2020-08-20 Published:2020-10-12
Contact: Xue-Qiang Wang
Supported by:
the Huxiang Young Talent Program from Hunan Province(2019RS2022)

1. cjoc20206077辅助材料.pdf(6638KB)

Abstract

A KOt-Bu empowered transition-metal free and efficient procedure for the etherification of alkoxy heteroarenes, heteroaryl halides and heteroaryl thioethers with various primary, secondary, tertiary aliphatic alcohols has been developed. The usefulness of our method is highlighted by the derivatization of natural products and bioactive molecules, and the synthesis of deuterated heteroaryl alkyl ethers that are not easy to access via other approaches.

Key words: etherification, heteroaryl alkyl ethers, nucleophilic aromatic substitution

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Xia Wang, Yixin Qu, Chengyu Long, Xue-Qiang Wang. Nucleophilic Etherification of Heteroaryl Alkyl Ethers, Heteroaryl Halides with (Deuterated) Alcohols[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 795-805.

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Fig. & Tab. 5

Figure 1. Representative ether containing anticancer drugs and the methods for heteroaryl ether synthesis.

Table 1. Scope of nucleofugesa

Table 2. Scope of methoxy heteroarenes and alcohols

Table 3. Derivatization of pharmaceuticals or bio-related molecules

Table 4. Scope of etherification of deuterated alcoholsa

References 16

[1]	Buckingham J. Dictionary of Natural Products, University Press, Cambridge, MA, 1994. pmid: 21643619
	(b) Evano G.; Wang J.; Nitelet A. Org. Chem. Front. 2017, 4, 2480. doi: 10.1039/C7QO00671C pmid: 21643619
	(c) Enthaler S.; Company A. Chem. Soc. Rev. 2011, 40, 4912. doi: 10.1039/c1cs15085e pmid: 21643619
	(d) Theil F. Angew. Chem. Int. Ed. 1999, 38, 2345. doi: 10.1002/(ISSN)1521-3773 pmid: 21643619
	(e) Muci A.R.; Buchwald S.L. Top. Curr. Chem. 2002, 219, 131. pmid: 21643619
	(f) Thomas A.W.; Ley S.V. Angew. Chem., Int. Ed. 2003, 42, 5400. doi: 10.1002/(ISSN)1521-3773 pmid: 21643619
[2]	(a) Manchado E.; Weissmueller S.; Morris J.P.; Chen C.C.; Wullenkord R.; Lujambio A.; Stanchina E.; Poirier J.T.; Gainor J.F.; Corcoran R.B.; Engelman J.A.; Rudin C.M.; Rosen N.; Lowe S.W. Nature 2016, 534, 647. pmid: 27338794
	(b) Huang S.; Hölzel M.; Knijnenburg T.; Schlicker A.; Roepman P.; McDermott U.; Garnett M.; Grernrum W.; Sun C.; Prahallad A.; Groenendijk F.H.; Mittempergher L.; Nijkamp W.; Neefjes J.; Salazar R.; Dijke P.; Uramoto H.; Tanaka F.; Beijersbergen R.L.; Wessels L.F.; Bernards R. Cell 2012, 151, 937. doi: 10.1016/j.cell.2012.10.035 pmid: 27338794
	(c) Wang S.; Cang S.; Liu D. J. Hematol. Oncol. 2016, 9, 34. doi: 10.1186/s13045-016-0268-z pmid: 27338794
[3]	Muci A.R.; Buchwald S.L. Practical Palladium Catalysts for C—N and C—O Bond Formation. In Topics in Current Chemistry, Ed.: Miyaura, N. E., Springer-Verlag, Berlin, Germany, 2001, Vol. 219, p. 131. pmid: 17973536
	Hartwig J.F. In Handbook of Organopalladium Chemistry for Organic Synthesis, Ed.: Negishi, E. E., Wiley-Interscience, New York, 2002, p. 1051. pmid: 17973536
	(c) Beletskaya I.P.; Cheprakov A.V. Coord. Chem. Rev. 2004, 248, 2337. doi: 10.1016/j.ccr.2004.09.014 pmid: 17973536
	(d) Bedford R.B.; Cazin C. S. J.; Holder D. Coord. Chem. Rev. 2004, 248, 2283. doi: 10.1016/j.ccr.2004.06.012 pmid: 17973536
	(e) Beccalli E.M.; Broggini G.; Martinelli M.; Sottocornola S. Chem. Rev. 2007, 107, 5318. pmid: 17973536
[4]	(a) Vorogushin A.V.; Huang X.; Buchwald S.L. J. Am. Chem. Soc. 2005, 127, 8146. pmid: 15926842
	(b) Zhang H.; Ruiz-Castillo P.; Buchwald S.L. Org. Lett. 2018, 20, 1580. doi: 10.1021/acs.orglett.8b00325 pmid: 15926842
[5]	Chen Z.; Jiang Y.; Zhang L.; Guo Y.; Ma D. J. Am. Chem. Soc. 2019, 141, 3541. doi: 10.1021/jacs.8b12142
[6]	Terrett J.A.; Cuthbertson J.D.; Shurtleff V.W.; MacMillan D. W. C.Nature 2015, 524, 330. doi: 10.1038/nature14875 pmid: 26266976
[7]	(a) Williamson A. Philos. Mag. 1850, 37, 299.
	(b) Fuhrmann E.; Talbiersky J. Org. Process Res. Dev. 2005, 9, 206. doi: 10.1021/op050001h
[8]	Swamy K. C. K.; Kumar N. N. B.; Balaraman E.; Kumar K. V. P.P.Chem. Rev. 2009, 109, 2551. doi: 10.1021/cr800278z
[9]	Caron S.; Ghosh A. Nucleophilic Aromatic Substitution. In Practical Synthetic Organic Chemistry Reactions Principles and Techniques, John Wiley & Sons, Hoboken, NJ, 2011, p. 237.
[10]	For representative publications: a Zarate, C.; Manzano, R.; Martin, R.J. Am. Chem. Soc. 2015, 137, 6754. doi: 10.1021/jacs.5b03955
	(b) Zarate C.; Nakajima M.; Martin R. J. Am. Chem. Soc. 2017, 139, 1191. doi: 10.1021/jacs.6b10998
	(c) Sergeev A.G.; Hartwig J.F. Science 2011, 332, 439. doi: 10.1126/science.1200437
	(d) Álvarez-Bercedo P.; Martin R. J. Am. Chem. Soc. 2010, 132, 17352. doi: 10.1021/ja106943q
	(e) Guan B.; Xiang S.; Wang B.; Sun Z.; Wang Y.; Zhao K.; Shi Z. J. Am. Chem. Soc. 2008, 130, 3268. doi: 10.1021/ja710944j
	(f) Guo L.; Liu X.; Baumann C.; Rueping M. Angew. Chem. Int. Ed. 2016, 55, 15415. doi: 10.1002/anie.v55.49
	(g) Liu X.; Hsiao C.C.; Kalvet I.; Leiendecker M.; Guo L.; Schoenebeck F.; Rueping M. Angew. Chem. Int. Ed. 2016, 55, 6093. doi: 10.1002/anie.v55.20
	(h) Cong X.; Tang H.; Zeng X. J. Am. Chem. Soc. 2015, 137, 14367. doi: 10.1021/jacs.5b08621
	(i) Tobisu M.; Takahira T.; Morioka T.; Chatani N. J. Am. Chem. Soc. 2016, 138, 6711. doi: 10.1021/jacs.6b03253
	(j) Wang X.; Li C.; Wang X.; Wang Q.; Dong X.; Duan A.; Zhao W. Org. Lett. 2018, 20, 4267. doi: 10.1021/acs.orglett.8b01696
	(k) Wang X.; Tang Y.; Long C.; Dong W.; Li C.; Xu X.; Zhao W.; Wang X. Org. Lett. 2018, 20, 4749. doi: 10.1021/acs.orglett.8b01758
	(l) Tang N.; Shao X.; Wang M.; Wu X.; Zhu C. Acta Chim. Sinica 2019, 77, 922. doi: 10.6023/A19050158
	(m) Huang S.; Nie Y.; Yang J.; Zheng Z.; Cao J.; Xu Z.; Xu L. Chin. J. Org. Chem. 2020, 40, 2018. doi: 10.6023/cjoc202003035
	(n) Tao X.; Sheng R.; Bao K.; Wang Y.; Jin Y. Chin. J. Org. Chem. 2019, 39, 2726. doi: 10.6023/cjoc201903063
[11]	(a) Kwan E.E.; Zeng Y.; Besser H.A.; Jacobsen E.N. Nat. Chem. 2018, 10, 917. doi: 10.1038/s41557-018-0079-7
	(b) Neumann C.N.; Ritter T. Acc. Chem. Res. 2017, 50, 2822. doi: 10.1021/acs.accounts.7b00413
	Terrier F. Modern Nucleophilic Aromatic Substitution, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2013.
[12]	Representative examples for quinoline containing ether type anticancer drugs: a Xie, C.; Wan, X.; Quan, H.; Zheng, M.; Fu, L.; Li, Y.; Lou, L.Cancer Sci. 2018, 109, 1207. doi: 10.1111/cas.2018.109.issue-4 pmid: 25617424
	(b) Wang T.; Xiao M.; Ge Y.; Krepler C.; Belser E.; Lopez-Coral A.; Xu X.; Zhang G.; Azuma R.; Liu Q.; Liu R.; Li L.; Amaravadi R.K.; Xu W.; Karakousis G.; T. Gangadhar, C.; Schuchter, L.M.; Lieu, M.; Khare, S.; Halloran, M.B.; Herlyn, M.; Kaufman, R.E.Clin. Cancer Res. 2015, 21, 1652. doi: 10.1158/1078-0432.CCR-14-1554 pmid: 25617424
[13]	Li F.; Fernandez P.P.; Rajendran P.; Hui K.M.; Sethi G. Cancer Lett. 2010, 292, 197. doi: 10.1016/j.canlet.2009.12.003
[14]	(a) DeVore N.M.; Scott E.E. Nature 2012, 482, 116. doi: 10.1038/nature10743 pmid: 28971491
	(b) Abedinpour P.; Baron V.T.; Chrastina A.; Rondeau G.; Pelayo J.; Welsh J.; Borgström P. Prostate 2017, 77, 1550. doi: 10.1002/pros.23428 pmid: 28971491
[15]	Richtand N.M.; Welge J.A.; Logue A.D.; Keck P.E.; Strakowski S.M.; McNamara R.K. Neuropsychopharmacology. 2007, 32, 1715. doi: 10.1038/sj.npp.1301305
[16]	(a) Atzrodt J.; Derdau V.; Kerr W.J.; Reid M. Angew. Chem., Int. Ed. 2018, 57, 1758. doi: 10.1002/anie.201704146
	(b) Gant T.G. J. Med. Chem. 2014, 57, 3595. doi: 10.1021/jm4007998
	(c) Pirali T.; Serafini M.; Cargnin S.; Genazzani A.A. J. Med. Chem. 2019, 62, 5276. doi: 10.1021/acs.jmedchem.8b01808
	(d) Chang Y.; Yesilcimen A.; Cao M.; Zhang Y.; Zhang B.; Chan J.Z.; Wasa M. J. Am. Chem. Soc. 2019, 141, 14570. doi: 10.1021/jacs.9b08662

杂芳基烷基醚、杂芳基卤化物与(氘代)醇的亲核醚化

Nucleophilic Etherification of Heteroaryl Alkyl Ethers, Heteroaryl Halides with (Deuterated) Alcohols

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Fig. & Tab. 5

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