Photo-catalyzed sequential dearomatization/carboxylation of benzyl o-halogenated aryl ether with CO2 leading to spirocyclic carboxylic acids

doi:10.1016/S1872-2067(21)63956-6

Abstract

Abstract:

Photo-catalyzed tandem dearomatization/carboxylation of benzyl o-halogenated aryl ether with CO₂ was achieved, which affords spirocyclic carboxylic acids under mild conditions. The reaction has good functional group tolerance with high yields. Mechanism studies indicate that the transformation was realized via intramolecular radical addition and nucleophilic addition.

Key words: Photocatalysis, Carbon dioxide, Dearomatization, Carboxylation, Spiro compounds

Yaping Yi, Chanjuan Xi. Photo-catalyzed sequential dearomatization/carboxylation of benzyl o-halogenated aryl ether with CO₂ leading to spirocyclic carboxylic acids[J]. Chinese Journal of Catalysis, 2022, 43(7): 1652-1656.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(21)63956-6

https://www.cjcatal.com/EN/Y2022/V43/I7/1652

Figures/Tables 5

Fig. 1. Synthesis of spiro compounds.

Table 1 Optimization of Reaction Conditions.


Entry	Deviation	Yield of 2a ^a(%)
1	None	76 (66)
2	DMF instead of DMSO	22
3	MeCN instead of DMSO	N.D.
4	Ir[dF(CF₃)ppy]₂(dtbpy)PF₆ instead of 4CzIPN	70
5	Ru(bpy)₃Cl₂·6H₂O instead of 4CzIPN	40
6	Et₃N instead of DIPEA	43
7	Cy₂NMe instead of DIPEA	12
8	Cs₂CO₃ instead of t-BuONa	64
9	2.0 equiv. of DIPEA	67
10	2.0 equiv. of t-BuONa	68
11	4CzIPN (2.5 mol%)	55
12	without CO₂	N.D.
13	without light	N.D.
14	without 4CzIPN	N.D.
15	without DIPEA	N.D.
16	without t-BuONa	20
17	Br instead of I in 1a	9
18	Cl instead of I in 1a	2

Scheme 1. Evaluation of substrate scope. Reaction conditions: 1a (0.2 mmol), 4CzIPN (5 mol%), DIPEA (0.6 mmol), t-BuONa (0.6 mmol), DMSO (2.0 mL), 1 atm CO2, 5 W Blue LED, room temperature, 12 h, quenched by HCl (2 mol/L), isolated yield. a The reaction time is extended to 24 h. b Quenched by HCl (2 mol/L), extraction, then TMSCHN2 (2.0 equiv. in 1.0 mL MeOH/Et2O, v/v = 1:1).

Scheme 2. Mechanism studies. (a) TEMPO was added in the reaction. (b) The reaction was treated without CO2 under N2 and the reaction mixture was quenched by the D2O. (c) Using DCl (2 mol/L) further quenched the reaction. (d) Stern-Volmer fluorescence quenching experiments.

Scheme 3. Proposed mechanism.

References

[1]	A. Baeyer, Ber. Dtsch. Chem. Ges., 1900, 33, 3771-3775.
[2]	Y. Zheng, C. M. Tice, S. B. Singh, Bioorg. Med. Chem. Lett., 2014, 24, 3673-3682.
[3]	K. Acosta-Quiroga, C. Rojas-Pena, L. S. Nerio, M. Gutierrez, E. Polo-Cuadrado, RSC Adv., 2021, 11, 21926-21954.
[4]	Q.-L. Zhou, J.-H. Xie, Asymmetric Catalysis from a Chinese Perspective, Springer, Berlin, Heidelberg, 2011, 1-28.
[5]	X. Wang, Z. Han, Z. Wang, K. Ding, Angew. Chem. Int. Ed., 2012, 51, 936-940.
[6]	J. Xie, Q. Zhou, Acta Chim. Sin., 2014, 72, 778-797.
[7]	C. Xu, W. Hu, Chem. J. Chin. Univ.-Chin., 2020, 41, 2153-2173.
[8]	G. Such, R. A. Evans, L. H. Yee, T. P. Davis, J. Macromol. Sci., Polym. Rev., 2003, 43, 547-579.
[9]	M. M. Youssef, M. A. Amin, Molecules, 2010, 15, 8827-8840.
[10]	H. Chen, H. Shang, Y. Liu, R. Guo, W. Lin, Adv. Funct. Mater., 2016, 26, 8128-8136.
[11]	S. Kotha, A. C. Deb, K. Lahiri, E. Manivannan, Synthesis, 2009, 165-193.
[12]	A. K. Franz, N. V. Hanhan, N. R. Ball-Jones, ACS Catal., 2013, 3, 540-553.
[13]	E. M. Carreira, T. C. Fessard, Chem. Rev., 2014, 114, 8257-8322.
[14]	P.-W. Xu, J.-S. Yu, C. Chen, Z.-Y. Cao, F. Zhou, J. Zhou, ACS Catal., 2019, 9, 1820-1882.
[15]	K. Babar, A. F. Zahoor, S. Ahmad, R. Akhtar, Mol. Divers., 2021, 25, 2487-2532.
[16]	Y. Hayashi, in: Cycloaddition Reactions in Organic Synthesis, S. Kobayashi, K. A. Jorgensen edt., Wiley-VCH, Weinheim, Germany, 2001, 5-55.
[17]	H. B. Hepburn, L. Dell’Amico, P. Melchiorre, Chem. Rec., 2016, 16, 1787-1806.
[18]	X. Companyo, A. Zea, A.-N. R. Alba, A. Mazzanti, A. Moyano, R. Rios, Chem. Commun., 2010, 46, 6953-6955.
[19]	B. Zhou, Y. Yang, J. Shi, Z. Luo, Y. Li, J. Org. Chem., 2013, 78, 2897-2907.
[20]	X. Han, W. Yao, T. Wang, Y. R. Tan, Z. Yan, J. Kwiatkowski, Y. Lu, Angew. Chem. Int. Ed., 2014, 53, 5643-5647.
[21]	D. Hack, A. B. Dürr, K. Deckers, P. Chauhan, N. Seling, L. Rübenach, L. Mertens, G. Raabe, F. Schoenebeck, D. Enders, Angew. Chem. Int. Ed., 2016, 55, 1797-1800.
[22]	B. Tan, N. R. Candeias, C. F. Barbas, Nat. Chem., 2011, 3, 473-477.
[23]	B. Xiang, K.M. Belyk, R. A. Reamer, N. Yasuda, Angew. Chem. Int. Ed., 2014, 53, 8375-8378.
[24]	B. F. Rahemtulla, H. F. Clark, M. D. Smith, Angew. Chem. Int. Ed., 2016, 55, 13180-13183.
[25]	K. Zhang, M. Meazza, V. Docekal, M. E. Light, J. Vesely, R. Rios, Eur. J. Org. Chem., 2017, 2017, 1749-1756.
[26]	C.-X. Zhuo, C. Zheng, S.-L. You, Acc. Chem. Res., 2014, 47, 2558-2573.
[27]	C. Zheng, S.-L. You, Chem, 2016, 1, 830-857.
[28]	Q. Gu, S. You, Chem. World, 2019, 60, 641-650.
[29]	W.-C. Yang, M.-M. Zhang, J.-G. Feng, Adv. Synth. Catal., 2020, 362, 4446-4461.
[30]	R. Pawlowski, P. Skorka, M. Stodulski, Adv. Synth. Catal., 2020, 362, 4462-4486.
[31]	M. Okumura, D. Sarlah, Eur. J. Org. Chem., 2020, 2020, 1259-1273.
[32]	B. Hu, Y. Li, W. Dong, K. Ren, X. Xie, J. Wan, Z. Zhang, Chem. Commun., 2016, 52, 3709-3712.
[33]	L. Huang, Y. Cai, H.-J. Zhang, C. Zheng, L.-X. Dai, S.-L. You, CCS Chem., 2019, 1, 106-116.
[34]	M. Zhu, C. Zheng, X. Zhang, S.-L. You, J. Am. Chem. Soc., 2019, 141, 2636-2644.
[35]	A. B. Rolka, B. Koenig, Org. Lett., 2020, 22, 5035-5040.
[36]	L. Wu, Y. Hao, Y. Liu, H. Song, Q. Wang, Chem. Commun., 2020, 56, 8436-8439.
[37]	M. Zhu, X.-L. Huang, H. Xu, X. Zhang, C. Zheng, S.-L. You, CCS Chem., 2021, 3, 652-664.
[38]	A. R. Flynn, K. A. McDaniel, M. E. Hughes, D. B. Vogt, N. T. Jui, J. Am. Chem. Soc., 2020, 142, 9163-9168.
[39]	Z. Fan, Z. Zhang, C. Xi, ChemSusChem, 2020, 13, 6201-6218.
[40]	B. Zhang, Y. Yi, Z.-Q. Wu, C. Chen, C. Xi, Green Chem., 2020, 22, 5961-5965.
[41]	Z. Fan, Y. Yi, S. Chen, C. Xi, Org. Lett., 2021, 23, 2303-2307.
[42]	T. Sakakura, J.-C. Choi, H. Yasuda, Chem. Rev., 2007, 107, 2365-2387.
[43]	M. Mikkelsen, M. Jørgensen, F. C. Krebs, Energy Environ. Sci., 2021, 3, 43-81.
[44]	M. Aresta, A. Dibenedetto, A. Angelini, Chem. Rev., 2014, 114, 1709-1742.
[45]	J. Artz, T. E. Müller, K. Thenert, J. Kleinekorte, R. Meys, A. Sternberg, A. Bardow, W. Leitner, Chem. Rev., 2018, 118, 434-504.
[46]	S.-S. Yan, Q. Fu, L.-L. Liao, G.-Q. Sun, J.-H. Ye, L. Gong, Y.-Z. Bo-Xue, D.-G. Yu, Coord. Chem. Rev., 2018, 374, 439-463.
[47]	S. Wang, C. Xi, Chem. Soc. Rev., 2019, 48, 382-404.
[48]	J. B. Hanuman, R. K. Bhatt, B. K. Sabata, Phytochemistry, 1986, 25, 1677-1680.
[49]	G. Fontana, G. Savona, B. Rodriguez, J. Nat. Prod., 2006, 69, 1734-1738.
[50]	Z.-H. Pan, J.-T. Cheng, J. He, Y.-Y. Wang, L.-Y. Peng, G. Xu, W.-B. Sun, Q.-S. Zhao, Helv. Chim. Acta, 2011, 94, 417-422.
[51]	Y. Gao, H. Wang, Z. Chi, L. Yang, C. Zhou, G. Li, CCS Chem., 2021, 3, 1848-1859.
[52]	J. B. Pedley, R. D. Naylor, S. P. Kirby, Thermochemical Data of Organic Compounds, 2nd ed., Chapman and Hall, New York, 1986.
[53]	R. Ishimatsu, S. Matsunami, T. Kasahara, J. Mizuno, T. Edura, C. Adachi, K. Nakano, T. Imato, Angew. Chem. Int. Ed., 2014, 53, 6993-6996.
[54]	M. Sayes, G. Benoit, A. B. Charette, Angew. Chem. Int. Ed., 2018, 57, 13514-13518.

Photo-catalyzed sequential dearomatization/carboxylation of benzyl o-halogenated aryl ether with CO₂ leading to spirocyclic carboxylic acids

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