SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

0 240910

DOI: https://doi.org/10.6023/cjo202405019

REVIEW

Metal-Catalyzed Hydrophosphinylation of Non-activated Alkynes: A Mechanistic Perspective

  • Yi-Yu Liu ,
  • Yudong Hu ,
  • Qing-Wei Zhang
Expand
  • Key Laboratory of Precision and Intelligent Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, 230026
Yi-Yu Liu (left) studies chemistry at the University of Science and Technology of China (2021.9 to present). She joined Qing-Wei Zhang's group in March 2023, focusing on asymmetric catalysis and mechanistic study. Yudong Hu (middle) studies chemistry at the University of Science and Technology of China (2021.9 to present). He joined Qing-Wei Zhang's group in November 2023, focusing on asymmetric catalysis and mechanistic study.Qing-Wei Zhang (right) graduated from Lanzhou University with a B.S. and PhD degree. He then worked as a postdoctoral researcher at Tsinghua University (2012.7-2015.1) and the University of California, Berkeley (2015.3-2018.3). In March 2018, he joined the University of Science and Technology of China as a principal investigator. His research interests are asymmetric catalysis and the development of novel chiral ligands. †These authors contributed equally to this work.

Received date: 2024-05-15

  Revised date: 2024-08-09

  Online published: 2024-09-10

Supported by

NSFC (No. 22071224)

Fold

Abstract

The synthesis of phosphine compounds through the addition reaction of H-[P(O)] species to olefins and alkynes has been extensively studied. This paper mainly summarizes two different mechanisms of the addition of H-[P(O)] species to non-activated alkyne. One is the oxidative addition-migration insertion-reductive elimination mechanism, namely the Chalk-Harrod type mechanism, and the other is the proton transfer-reductive elimination mechanism. This article elaborates on the specific steps of each mechanism and discusses experimental and computational evidence supporting these steps. Additionally, a few other types of mechanisms are briefly mentioned. The mechanism of H-[P(O)] reaction with relevant conjugated dienes was also involved when closely related.

Key words： H-P(O) addition; mechanistic study; Chalk-Harrod type mechanism; proton transfer; ligand to ligand hydrogen transfer

Cite this article

Yi-Yu Liu , Yudong Hu , Qing-Wei Zhang . Metal-Catalyzed Hydrophosphinylation of Non-activated Alkynes: A Mechanistic Perspective[J]. Chinese Journal of Organic Chemistry, 0 : 240910 . DOI: 10.6023/cjo202405019

References

[1](a) Guo H.; Fan Y. C.; Sun Z.; Wu Y.; Kwon O. Chem. Rev.2018, 118, 10049-10293.
(b) Ni H.; Chan W.-L.; Lu Y. Chem. Rev.2018, 118, 9344-9411.
(c) Liu X., Wu Y., Zhang Q. Synlett2022, 33, 301-306.
(d) Banerjee I, Panda TK. Org Biomol Chem.2021, 19(30), 6571-6587.
(e) B. T. Novas, R. Waterman, ChemCatChem.2022, 14, e20220098.
[2]Han, L.-B.; Tanaka, M.,J. Am. Chem. Soc. 1996, 118 (6), 1571-1572.
[3]Han, L.-B.; Choi, N.; Tanaka, M.,Organometallics 1996, 15 (15), 3259-3261.
[4]Han L.-B.; Mirzaei F.; Zhao C.-Q.; Tanaka, M., J. Am. Chem. Soc.2000, 122 (22), 5407-5408.
[5]Zhao, C.-Q.; Han, L.-B.; Tanaka, M.,Organometallics 2000, 19 (21), 4196-4198.
[6]Dobashi, N.; Fuse, K.; Hoshino, T.; Kanada, J.; Kashiwabara, T.; Kobata, C.; Nune, S. K.; Tanaka, M.,Tetrahedron Lett. 2007, 48 (27), 4669-4673.
[7]Zhao, C.-Q.; Han, L.-B.; Goto, M.; Tanaka, M.,Angew Chem Int Ed. 2001, 40 (10), 1929-1932.
[8]Han, L.-B.; Zhao, C.-Q.; Tanaka, M.,J. Org. Chem. 2001, 66 (17), 5929-5932.
[9]Han L.-B.; Zhang C.; Yazawa H.; Shimada, S., J. Am. Chem. Soc.2004, 126 (16), 5080-5081.
[10]Khemchyan, L. L.; Ivanova, J. V.; Zalesskiy, S. S.; Ananikov, V. P.; Beletskaya, I. P.; Starikova, Z. A.,Adv. Synth. Catal. 2014, 356 (4), 771-780.
[11]Zhang, Y.-Q.; Han, X.-Y.; Wu, Y.; Qi, P.-J.; Zhang, Q.; Zhang, Q.-W.,Chem. Sci. 2022, 13 (14), 4095-4102.
[12]Yang, S.-N.; Sun, S.-H.; Liu, C.-H.; Min, X.-T.; Wan, B.; Ji, D.-W.; Chen, Q.-A.,Chin. Chem. Lett. 2023, 34 (6), 107914.
[13]Qian, D.-W.; Yang, J.; Wang, G.-W.; Yang, S.-D.,J. Org. Chem. 2023, 88 (6), 3539-3554.
[14]Niu, M.; Fu, H.; Jiang, Y.; Zhao, Y., Chem. Commun. 2007, (3), 272-274.
[15]Liu, L. L.; Wu, Y.; Wang, Z.; Zhu, J.; Zhao, Y.,J. Org. Chem. 2014, 79 (15), 6816-6822.
[16]Li, J.; Gao, Z.; Guo, Y.; Liu, H.; Zhao, P.; Bi, X.; Shi, E.; Xiao, J.,RSC Adv. 2022, 12 (29), 18889-18896.
[17]Wu, Z.-H.; Cheng, A.-Q.; Yuan, M.; Zhao, Y.-X.; Yang, H.-L.; Wei, L.-H.; Wang, H.-Y.; Wang, T.; Zhang, Z.; Duan, W.-L.,Angew Chem Int Ed. 2021, 60 (52), 27241-27246.
[18]Nie S.-Z.; Davison R. T.; Dong, V. M., J. Am. Chem. Soc.2018, 140 (48), 16450-16454.
[19]Yang, Z.; Wang, J.,Angew Chem Int Ed. 2021, 60 (52), 27288-27292.
[20]Zhou, J.; Meng, L.; Lin, S.; Cai, B.; Wang, J.,Angew Chem Int Ed. 2023, 62 (26), e202303727.
[21]Long, J.; Li, Y.; Zhao, W.; Yin, G.,Chem. Sci. 2022, 13 (5), 1390-1397.
[22]Han L.-B.; Zhao C.-Q.; Onozawa S.-y.; Goto M.; Tanaka, M., J. Am. Chem. Soc.2002, 124 (15), 3842-3843.
[23]Dai, Q.; Liu, L.; Qian, Y.; Li, W.; Zhang, J.,Angew Chem Int Ed. 2020, 59 (46), 20645-20650.
[24]Yang, Z.; Gu, X.; Han, L.-B.; Wang, J.,Chem. Sci. 2020, 11 (28), 7451-7455.
[25](a) Xu Q.; Han, L.-B., J. Organomet. Chem.2011, 696 (1), 130-140.
(b) Ding, K.; Su, B.,Eur. J. Org. Chem. 2024, 27 (4), e202301160.
[26](a) Rosenberg, L. ACS Catal. 2013, 3 (12), 2845-2855.
(b) Lecerclé D.; Sawicki M.; Taran, F. Org. Lett.2006, 8 (19), 4283-4285.
[27](a) Glueck, D. S. Top. Organomet. Chem.2010, 31, 65-100.
(b) V.Koshti, S. Gaikwad, S. H.Chikkali, Coord.Chem.Rev.2014, 265, 52-73.
(c) C. A. Bange, R. Waterman, Chem. Eur. J. 2016, 22, 12598.
(d) Samantha Lau, Thomas M. Hood, and Ruth L. Webster, ACS Catal. 2022, 12 (17), 10939-10949.
[28]Chen T.; Zhao C.-Q.; Han, L.-B., J. Am. Chem. Soc.2018, 140 (8), 3139-3155.
[29]Liu, S.-Y.; Li, Z.-M.; Guo, H.; Zhang, J.-L.,Eur. J. Org. Chem. 2023, 26 (44), e202300804.
[30]Chen T, Han L-B. Heteroatom Chem. 2018, 29, e21460.
[31]Glueck, D. S. J. Org. Chem.2020, 85, 14276-14285.
[32]Han, L.-B.; Hua, R.; Tanaka, M.,Angew Chem Int Ed. 1998, 37 (1-2), 94-96.
[33]Shen R.; Chen T.; Zhao Y.; Qiu R.; Zhou Y.; Yin S.; Wang X.; Goto M.; Han, L.-B. J. Am. Chem. Soc.2011, 133, 17037.
[34]Jiang, Y.-Y.; Fan, X.; Li, Y.; Ji, G.-C.; Liu, P.; Bi, S.,J. Org. Chem. 2022, 87 (21), 14673-14684.
[35]Chen T, Liu L, Huang T, Han L.-B. Chin. J. Org. Chem., 2019, 39 (8), 2183-2187.
[36](a) J. Gu, C. Cai, Org. Biomol. Chem. 2017, 15, 4226-4230.
(b) X. Chen, X. Chen, X. Li, C. Qu, L. Qu, W. Bi, K. Sun, Y. Zhao, Tetrahedron.2017, 73, 2439-2446.
(c) Liu WQ, Lei T, Zhou S, et al. J. Am. Chem. Soc.2019, 141, 13941-7.
[37](a) Wang H, Li Y, Tang Z, et al. ACS Catal.2018, 8, 10599-605.
(b) H. Hou, J. Wang, X. Chen, Y. Han, H. Yu, C. Yan, Y. Shi, S. Zhu, ChemCatChem.2022, 14, e202201073.
[38]Yoo W, Kobayashi S., Green Chem. 2013, 15, 1844.
[39](a) Jin S, Sun S, Yu JT, Cheng J., J. Org. Chem. 2019, 84, 11177-85.
(b) Hou H, Xu Y, Yang H, et al., Org. Lett. 2020, 22, 1748-53.
[40]X. Chen, X. Li, X. Chen, L. Qu, J. Chen, K. Sun, Z. Liu, W. Bi, Y. Xia, H. Wua,Y. Zhao, Chem. Commun. 2015, 51, 3846-3849.
[41](a) Liu J, Xiao HZ, Fu Q, Yu DG. Chem. Synth. 2021, 1, 9.
(b) Y. Yuan, C. Darcel, ChemCatChem. 2024, e202400703.
Options
Outlines

/

〈 〉