Hiyama Cross-Coupling Reaction of Aryl Vinylsilanes and Aryl Halides

doi:10.6023/cjoc202306025

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (10): 3614-3622.DOI: 10.6023/cjoc202306025 Previous Articles Next Articles

Special Issue: 有机硅化学专辑-2023

芳基乙烯基硅烷与芳基卤代物的Hiyama偶联反应

马伟源^a, 戴惠芳^b, 亢少林^a, 张天麟^a, 舒兴中^a^,^*()

a 兰州大学功能有机分子化学国家重点实验室兰州 73000
b 复旦大学药学院上海 201203

收稿日期:2023-06-28 修回日期:2023-07-23 发布日期:2023-08-16
作者简介:
† 共同第一作者
基金资助:
国家自然科学基金(22071084); 国家自然科学基金(22271127); 中央高校基本科研业务费专项资金(lzujbky-2022-ey01)

Hiyama Cross-Coupling Reaction of Aryl Vinylsilanes and Aryl Halides

Wei-Yuan Ma^a, Huifang Dai^b, Shaolin Kang^a, Tianlin Zhang^a, Xing-Zhong Shu^a()

a State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000
b School of Pharmacy, Fudan University, Shanghai 201203

Received:2023-06-28 Revised:2023-07-23 Published:2023-08-16
Contact: *E-mail: shuxingzh@lzu.edu.cn
About author:
† These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(22071084); National Natural Science Foundation of China(22271127); Fundamental Research Funds for the Central Universities(lzujbky-2022-ey01)

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Abstract

The Hiyama coupling reaction has emerged as a wildly used method for the construction of C—C bonds, especially in the fields of aryl-aryl and aryl-alkenyl coupling reactions. In general, this protocol highly relies on reactive but unstable silicon reagents such as R—SiF₃ and R—Si(OMe)₃. The development of Hiyama coupling reaction involving stable organosilanes is in high demand. In this manuscript, a palladium-catalyzed cross-coupling reaction of aryl vinylsilanes and aryl halides is reported, leading to the formation of Ar—Ar bonds. The reaction has shown good functional group compatibility and offered convenient access to biaryl compounds.

Key words: Hiyama reaction, cross-coupling reaction, aryl vinylsilanes, arylation, biaryl compounds

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Wei-Yuan Ma, Huifang Dai, Shaolin Kang, Tianlin Zhang, Xing-Zhong Shu. Hiyama Cross-Coupling Reaction of Aryl Vinylsilanes and Aryl Halides[J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3614-3622.

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Fig. & Tab. 6

Scheme 1. Transition-metal-catalyzed cross-coupling of organosilanes

Entry	Change of conditions	Yield/% of 3a
1	None	89 (85)^c
2	Pd(PPh₃)₂Cl₂^b	60
3	Pd(dba)₂^b	35
4	PdCl₂^b	15
5	CuCl	28
6	CuF₂	22
7	CsF	51
8	KF	19
9	No Pd, F, or Cu	0
10	PhBr was used^d	88^c

Table 1. Optimization of reaction conditionsa

Table 2. Substrates scope of aryl iodides and bromidesa

Table 3. Substrate scope of aryl vinylsilanesa

Table 4. Reactions with aryl chloridesa

Scheme 2. Proposed mechanism

References 36

[1]	(a) Thomson R. H. The Chemistry of Natural Products, Blackie and Son, Glasgow, UK, 1985.
	(b) Brunel J. M. Chem. Rev. 2005, 105, 857. doi: 10.1021/cr040079g
	(c) Corbet J. P.; Mignani G. Chem. Rev. 2006, 106, 2651. doi: 10.1021/cr0505268
[2]	(a) Nakao Y.; Hiyama T. Chem. Soc. Rev. 2011, 40, 4893. doi: 10.1039/c1cs15122c
	(b) Komiyama T.; Minami Y.; Hiyama T. ACS Catal. 2017, 7, 631. doi: 10.1021/acscatal.6b02374
[3]	(a) Chan T. H.; Fleming I. Synthesis 1979, 761. pmid: 26478695
	(b) Denmark S. E.; Ambrosi A. Org. Process Res. Dev. 2015, 19, 982. pmid: 26478695
[4]	(a) Hiyama T.; Oestreich M. Organosilicon Chemistry: Novel Approaches and Reactions, Wiley-VCH, Weinheim, 2019.
	(b) Denmark S. E.; Regens C. S. Acc. Chem. Res. 2008, 41, 1486. doi: 10.1021/ar800037p
	(c) Sore H. F.; Galloway W. R. J. D.; Spring D. R. Chem. Soc. Rev. 2012, 41, 1845. doi: 10.1039/C1CS15181A
	(d) Foubelo F.; Nájera C.; Yus M. Chem. Rec. 2016, 16, 2521. doi: 10.1002/tcr.v16.6
[5]	(a) Minami Y.; Hiyama T. Chem.-Eur. J. 2019, 25, 391. doi: 10.1002/chem.v25.2
	(b) Komiyama T.; Minami Y.; Hiyama T. Synlett 2017, 28,1873
[6]	(a) Duan J.; Wang K.; Xu G.-L.; Kang S.; Qi L.; Liu X.-Y.; Shu X.-Z. Angew. Chem., Int. Ed. 2020, 59, 23083. doi: 10.1002/anie.v59.51
	(b) Duan J.; Wang Y.; Qi L.; Guo P.; Pang X.; Shu X.-Z. Org. Lett. 2021, 23, 7855. doi: 10.1021/acs.orglett.1c02874
[7]	(a) Itami K.; Nokami T.; Yoshida J.-I. J. Am. Chem. Soc. 2001, 123, 5600. pmid: 36817085
	(b) Bergueiro J.; Montenegro J.; Cambeiro F.; Saá C.; López S. Chem.-Eur. J. 2012, 18, 4401. doi: 10.1002/chem.201103360 pmid: 36817085
	(c) Hosoi K.; Nozaki K.; Hiyama T. Chem. Lett. 2002, 31, 138. doi: 10.1246/cl.2002.138 pmid: 36817085
	(d) Vitale M.; Prestat G.; Lopes D.; Madec D.; Kammerer C.; Poli G.; Girnita L. J. Org. Chem. 2008, 73, 5795. doi: 10.1021/jo800707q pmid: 36817085
	(e) Lorion M. M.; Matt B.; Alves S.; Proust A.; Poli G.; Oble J.; Izzet G. Chem.-Eur. J. 2013, 19, 12607. doi: 10.1002/chem.v19.38 pmid: 36817085
	(f) Katayama H.; Nagao M.; Ozawa F.; Ikegami M.; Arai T. J. Org. Chem. 2006, 71, 2699. doi: 10.1021/jo052602c pmid: 36817085
	(g) Anderson J. C.; Munday R. H. J. Org. Chem. 2004, 69, 8971. pmid: 36817085
	(h) Pawley S. B.; Conner A. M.; Omer H. M.; Watson D. A. ACS Catal. 2022, 12, 13108. doi: 10.1021/acscatal.2c03981 pmid: 36817085
[8]	(a) Grushin V. V.; Alper H. Chem. Rev. 1994, 94, 1047. doi: 10.1021/cr00028a008
	(b) Littke A. F.; Fu G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
	(c) Yuen O. Y.; So C. M.; Man H. W.; Kwong F. Y. Chem.-Eur. J. 2016, 22, 6471. doi: 10.1002/chem.v22.19
[9]	Pierrat P.; Gros P.; Fort Y. Org. Lett. 2005, 7, 697. doi: 10.1021/ol047482u
[10]	(a) Lühning L. H.; Rosien M.; Doye S. Synlett 2017, 28, 2489. doi: 10.1055/s-0036-1589048
	(b) Kratz T.; Steinbach P.; Breitenlechner S.; Storch G.; Bann- warth C.; Bach T. J. Am. Chem. Soc. 2022, 144, 10133. doi: 10.1021/jacs.2c02511
[11]	Morioka T.; Nishizawa A.; Furukawa T.; Tobisu M.; Chatani N. J. Am. Chem. Soc. 2017, 139, 1416. doi: 10.1021/jacs.6b12293
[12]	Cao Z.-C.; Luo Q.-Y.; Shi Z.-J. Org. Lett. 2016, 18, 5978. doi: 10.1021/acs.orglett.6b02656
[13]	Guan B.-T.; Wang Y.; Li B.-J.; Yu D.-G.; Shi Z.-J. J. Am. Chem. Soc. 2008, 130, 14468. doi: 10.1021/ja8056503
[14]	Chen H.; Huang Z.; Hu X.; Tang G.; Xu P.; Zhao Y.; Cheng C.-H. J. Org. Chem. 2011, 76, 2338. doi: 10.1021/jo2000034 pmid: 21388215
[15]	Hua X.; Masson-Makdissi J.; Sullivan R. J.; Newman S. G. Org. Lett. 2016, 18, 5312. doi: 10.1021/acs.orglett.6b02631
[16]	Qin C.; Lu W. J. Org. Chem. 2008, 73, 7424. doi: 10.1021/jo801345b
[17]	Zhao C.-W.; Ma J.-P.; Liu Q.-K.; Yu Y.; Wang P.; Li Y.-A.; Wang K.; Dong Y.-B. Green Chem. 2013, 15, 3150. doi: 10.1039/c3gc41154k
[18]	Vila C.; Cembellín S.; Hornillos V.; Giannerini M.; Fañanás- Mastral M.; Feringa B. L. Eur. J. Org. Chem. 2015, 21, 15520.
[19]	Zhu S.; Xiao Y.; Guo Z.; Jiang H. Org. Lett. 2013, 15, 898. doi: 10.1021/ol4000394
[20]	Minami H.; Wang X.; Wang C.; Uchiyama M. Eur. J. Org. Chem. 2013, 2013, 7891. doi: 10.1002/ejoc.v2013.35
[21]	Mohamed R. K.; Mondal S.; Gold B.; Evoniuk C. J.; Banerjee T.; Hanson K.; Alabugin I. V. J. Am. Chem. Soc. 2015, 137, 6335. doi: 10.1021/jacs.5b02373 pmid: 25906261
[22]	Baxendale I. R.; Griffiths-Jones C. M.; Ley S. V.; Tranmer G. K. Chem.-Eur. J. 2006, 12, 4407. pmid: 16586523
[23]	Liang Z.; Ju L.; Xie Y.; Huang L.; Zhang Y. Chem.-Eur. J. 2012, 18, 15816. doi: 10.1002/chem.v18.49
[24]	Reddy V. P.; Qiu R.; Iwasaki T.; Kambe N. Org. Lett. 2013, 15, 1290. doi: 10.1021/ol400230y
[25]	Ye M.; Gao G.-L.; Edmunds A. J. F.; Worthington P. A.; Morris J. A.; Yu J.-Q. J. Am. Chem. Soc. 2011, 133, 19090. doi: 10.1021/ja209510q
[26]	Kaur M.; U Din Reshi N.; Patra K.; Bhattacherya A.; Kunnikuruvan S.; Bera J. K. Chem.-Eur. J. 2021, 27, 10737. doi: 10.1002/chem.v27.41
[27]	Budén M. E.; Guastavino J. F.; Rossi R. A. Org. Lett. 2013, 15, 1174. doi: 10.1021/ol3034687
[28]	Pan C.; Zhu J.; Chen R.; Yu J.-T. Org. Biomol. Chem. 2017, 15, 6467. doi: 10.1039/C7OB01564J
[29]	Pavia C.; Ballerini E.; Bivona L. A.; Giacalone F.; Aprile C.; Vaccaro L.; Gruttadauria M. Adv. Synth. Catal. 2013, 355, 2007. doi: 10.1002/adsc.v355.10
[30]	Gu P.; Xu Q.; Shi M. Synlett 2013, 24, 1255. doi: 10.1055/s-00000083
[31]	Mowery M. E.; DeShong P. J. Org. Chem. 1999, 64, 3266. pmid: 11674429
[32]	Salanouve E.; Bouzemame G.; Blanchard S.; Derat E.; Murr M. D.-E.; Fensterbank L. Chem.-Eur. J. 2014, 20, 4754. doi: 10.1002/chem.201304459 pmid: 24634349
[33]	Liang Q.; Xing P.; Huang Z.; Dong J.; Sharpless K. B.; Li X.; Jiang B. Org. Lett. 2015, 17, 1942. doi: 10.1021/acs.orglett.5b00654
[34]	Witzel S.; Xie J.; Rudolph M.; Hashmi A. S. K. Adv. Synth. Catal. 2017, 359, 1522. doi: 10.1002/adsc.v359.9
[35]	Wang D.-Y.; Wang C.; Uchiyama M. J. Am. Chem. Soc. 2015, 137, 10488. doi: 10.1021/jacs.5b06587
[36]	Shrestha B.; Thapa S.; Gurung S. K.; Pike R. A. S.; Giri R. J. Org. Chem. 2016, 81, 787. doi: 10.1021/acs.joc.5b02077

芳基乙烯基硅烷与芳基卤代物的Hiyama偶联反应

Hiyama Cross-Coupling Reaction of Aryl Vinylsilanes and Aryl Halides

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Fig. & Tab. 6

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