Supported Recyclable Metal-free Frustrated Lewis Pair Catalyst for Catalytic Hydrogenation of Substituted Pyridines to Piperidines

Shaohua Ma , Zhiyong Tang

Chemical Research in Chinese Universities ›› 2024, Vol. 40 ›› Issue (4) : 682 -689.

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Chemical Research in Chinese Universities ›› 2024, Vol. 40 ›› Issue (4) : 682 -689. DOI: 10.1007/s40242-024-4129-y
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Supported Recyclable Metal-free Frustrated Lewis Pair Catalyst for Catalytic Hydrogenation of Substituted Pyridines to Piperidines

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Abstract

The construction of heterogeneous frustrated Lewis pairs (FLPs) catalysts is crucial for realizing highly efficient and recyclable pyridines catalytic hydrogenation. In this work, we prepared a recyclable heterogenous FLPs catalyst CMP-BF with conjugated microporous polymer CMP-ethynyl as the support via self-catalyzed 1,1-carboboration reaction with commercial Lewis acid B(C6F5)3. The as-synthesized CMP-BF demonstrates superior heterogenous catalytic hydrogenation performance (conversion>99%), and considerable stability (84% conversion after three cycles) in recyclable hydrogenation of 2,6-phenylpyridine. This work provides insights into the fabrication and catalytic application of recyclable heterogenous FLP catalysts.

Keywords

Pyridine hydrogenation / Frustrated Lewis pair / Conjugated microporous polymer

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Shaohua Ma, Zhiyong Tang. Supported Recyclable Metal-free Frustrated Lewis Pair Catalyst for Catalytic Hydrogenation of Substituted Pyridines to Piperidines. Chemical Research in Chinese Universities, 2024, 40(4): 682-689 DOI:10.1007/s40242-024-4129-y

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References

[1]

Vitaku E, Smith D T, Njardarson J T. J. Med. Chem., 2014, 57: 10257.

[2]

Bhutani P, Joshi G, Raja N, Bachhav N, Rajanna P K, Bhutani H, Paul A T, Kumar R. J. Med. Chem., 2021, 64: 2339.

[3]

Gunasekar R, Goodyear R L, Silvestri I P, Xiao J L. Org. Biomol. Chem., 2022, 20: 1794.

[4]

Stephan D W, Erker G. Angew. Chem. Int. Ed., 2010, 49: 46.

[5]

Mahdi T, del Castillo J N, Stephan D W. Organometallics, 2013, 32: 1971.

[6]

Geier S J, Gille A L, Gilbert T M, Stephan D W. Inorg. Chem., 2009, 48: 10466.

[7]

Liu Y B, Du H F. J. Am. Chem. Soc., 2013, 135: 12968.

[8]

Scott D J, Simmons T R, Lawrence E J, Wildgoose G G, Fuchter M J, Ashley A E. ACS Catal., 2015, 5: 5540.

[9]

Ma Y Y, Zhang S, Chang C R, Huang Z Q, Ho J C, Qu Y Q. Chem. Soc. Rev., 2018, 47: 5541.

[10]

Zhang Y, Guo J, VanNatta P, Jiang Y, Phipps J, Roknuzzaman R, Rabaa H, Tan K, AlShahrani T, Ma S Q. J. Am. Chem. Soc., 2024, 146: 979.

[11]

Zhang Y, Chen S B, Al-Enizi A M, Nafady A, Tang Z Y, Ma S Q. Angew. Chem. Int. Ed. Engl., 2022, 62: e202213399.

[12]

Niu Z, Gunatilleke W D C B, Sun Q, Lan P C, Perman J, Ma J-G, Cheng Y C, Aguila B, Ma S Q. Chem, 2018, 4: 2587.

[13]

Niu Z, Zhang W J, Lan P C, Aguila B, Ma S Q. Angew. Chem. Int. Ed., 2019, 58: 7420.

[14]

Jiang J-X, Su F B, Trewin A, Wood C D, Niu H J, Jones J T A, Khimyak Y Z, Cooper A I. J. Am. Chem. Soc., 2008, 130: 7710.

[15]

Zhou Y B, Wang Y Q, Ning L C, Ding Z C, Wang W L, Ding C K, Li R H, Chen J J, Lu X, Ding Y J, Zhan Z P. J. Am. Chem. Soc., 2017, 139: 3966.

[16]

Chernichenko K, Madarasz A, Papai I, Nieger M, Leskela M, Repo T. Nat. Chem., 2013, 5: 718.

[17]

Ye J Y, McEwen M. J. Phys. Chem. A, 2022, 126: 18605.

[18]

Bergquist C, Bridgewater B M, Harlan C J, Norton J R, Friesner R A, Parkin G. J. Am. Chem. Soc., 2000, 122: 10581.

[19]

Mahdi T, Stephan D W. J. Am. Chem. Soc., 2014, 136: 15809.

[20]

Marques L R, Ando R A. Chemphyschem, 2023, 24: e202200715.

[21]

Ran Y, Yu X L, Liu J Q, Cui J Y, Wang J P, Wang L, Zhang Y H, Xiang X, Ye J H. J. Mater. Chem. A, 2020, 8: 13292.

[22]

Caputo C B, Geier S J, Winkelhaus D, Mitzel N W, Vukotic V N, Loeb S J, Stephan D W. Dalton Trans., 2012, 41: 2131.

[23]

özgün T, Ye K Y, Daniliuc C G, Wibbeling B, Liu L, Grimme S, Kehr G, Erker G. Chem. Eur. J., 201, 22: 5988.

[24]

Sivaev I B, Bregadze V I. Coord. Chem. Rev., 2014, 270/271: 75.

[25]

Beringhelli T, Donghi D, Maggioni D, D’Alfonso G. Coord. Chem. Rev., 2008, 252: 2292.

[26]

Reddy J S, Xu B-H, Mahdi T, Froehlich R, Kehr G, Stephan D W, Erker G. Organometallics, 2012, 31: 5638.

[27]

Wang J H, Wang G, Wang W Q, Zhang Z S, Liu Z T, Hao Z P. J. Mater. Chem. A, 2014, 2: 14028.

[28]

Ou J L, Zhao T X, Xiong W J, Liang H, Liu Q, Hu X B. Chem. Eng. J., 2023, 477: 147248.

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