Recent Development of Samarium Diiodide and Other Samarium Reagents in Organic Transformation

doi:10.6023/cjoc202011034

Abstract

Since the samarium diiodide was discovered, it has been occupying a key field in organic synthesis due to the excellent ability of both single electron transfer and reduction. Other samarium reagents have also been wildly developed in recent years, such as Sm, allylSmBr, SmI₃and so on. In this review, the reactions mediated by samarium reagents especially SmI₂ in latest five years are summarized. It mainly includes three parts: studies on the SmI₂ promoted coupling reactions, studies on the coupling reactions promoted by other samarium reagents (Sm, allylSmBr, SmI₃, Sm(OTf)₃ etc.), and studies on the samarium reagents promoted organic reduction reactions.

Key words: organic synthesis, coupling reactions, reductions, samarium diiodide, samarium reagents, organosamarium

Cite this article

Chen Liu, Yan Qi, Yongjun Liu. Recent Development of Samarium Diiodide and Other Samarium Reagents in Organic Transformation[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2202-2216.

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Fig. & Tab. 60

Scheme 1. Review of the coupling reactions of SmI2

Scheme 2. Synthetic Fig. of ryanodine

Scheme 3. SmI2-mediated radical cyclization cascade

Scheme 4. Catalytic cycle

Scheme 5. Ester with DIBAL-H and radical cyclization

Scheme 6. Construction of ABC ring of paclitaxel

Scheme 7. Mechanism for reductive coupling of nitrones and carbonyl compounds

Scheme 8. Alkylation of aniline derivatives or alkylation of heteroaromatic amines with various primary alcohols

Scheme 9. Cyclization of five-membered cyclic imides via aminoketyl radicals using SmI2-H2O

Scheme 10. SmI2-mediated synthesis of substituted alcohol

Scheme 11. Reaction of oxime ethers with SmI2

Scheme 12. Synthesis of α-aryl-α'-hydroxy ketones

Scheme 13. SmI2-LiBr mediated reductive coupling reactions

Scheme 14. SmI2-mediated spirocyclization reaction

Scheme 15. Radical cyclization

Scheme 16. Plausible transition states of radical cyclization

Scheme 17. SmI2 mediated asymmetric synthesis

Scheme 18. Radical cyclization of bromoalkyne with SmI2

Scheme 19. Synthesis of pyrrole

Scheme 20. Synthesis of 2,2'-biflavanones

Scheme 21. Hydrosilylation of alkynes

Scheme 22. The transformation of Pinacol

Scheme 23. Pinacol couplings of aliphatic aldehydes and ketones

Scheme 24. Construction of ABC ring of paclitaxel

Scheme 25. The transformation of Barbier

Scheme 26. SmI2-mediated furanosides coupling with cyclohexanone and octanal

Scheme 27. The mechanism of Refomatsky

Scheme 28. Intramolecular Reformatsky aldol cyclization

Scheme 29. Diastereoselective hydroxyethylation of β-hydroxyketones

Scheme 30. SmI2-mediated Reformatsky reaction of oxazolidinones with terpene enals

Scheme 31. Synthesis of tricyclo[5.2.1.01.6]decene

Scheme 32. SmI2-H2O in radical cyclization of five-membered lactones

Scheme 33. SmI2-mediated synthesis of dihydrothiochroman-ols

Scheme 34. SmI2-mediated reductive coupling dimerization

Scheme 35. SmI2-mediated desymmetrizing ketyl olefin cyclization

Scheme 36. SmI2-mediated reductive cyclization

Scheme 37. Homocoupling of benzyl halides

Scheme 38. Henry reactions with various aldehydes and nitroalkanes

Scheme 39. Addition of benzaldehydes to acrylates or maleates

Scheme 40. Promotion of the formation of MeOH by 4Å molecular sieves

Scheme 41. The versatile homocoupling of organohalides

Scheme 42. AllylSmBr mediated reaction of cyclization

Scheme 43. Reductive coupling of aldehydes or ketones with allylSmBr

Scheme 44. Synthesis of oxobicyclo[3.1.0]hexane-1-ols

Scheme 45. Michael addition of α-oxy ketones

Scheme 46. Sm(OTf)3 catalyzed [2+2+1] annulations of symmetric stilbenes with azidomethyl aromatics

Scheme 47. Recyclization of 1-oxa-3,6-dithiacycloheptane with amino acid esters

Scheme 48. SmI3 and I2 co-catalyzed aerobic α-hydroxylation of 1,3-dicarbonyl esters

Scheme 49. Reactions of α-haloketones promoted by SmI 3/CuI

Scheme 50. Aromatic or heterocyclic iodides and bromides coupling with ketone or aldehydes

Scheme 51. Reduction of selenoamide

Scheme 52. Enamine reduction

Scheme 53. Allylic benzoate reductions

Scheme 54. Deprotection using SmBr2

References 72

[1]	(a) Gansaüer, A.; Blum, H. Chem. Rev. 2000, 100,2771.
	(b) Gansaüer, A.; Lauterbach, T.; Narayan, S. Angew. Chem. Int. Ed. 2003, 42,5556.
	(c) Cuerva, J. M.; Justicia, J.; Oller-López, J. L.; Oltra, J. E. Top. Curr. Chem. 2006, 264,63.
	(d) Justicia, J.; Álvarez de Cienfuegos, L.; Cuerva, J. M. Chem. Soc. Rev. 2011, 40,3525.
	(e) Streuff, J. Synthesis 2013, 45,281.
[2]	(a) Shabangi, M.; Flowers, R. A. II Tetrahedron Lett. 1997, 38,1137.
	(b) Fuchs, J. R.; Mitchell, M. L.; Shabangi, M.; Flowers, R. A. II Tetrahedron Lett. 1997, 38,8157.
	(c) Shabangi, M.; Sealy, J. M.; Fuchs, J. R.; Flowers, R. A. II Tetrahedron Lett. 1998, 39,4429.
[3]	Procter, D. J.; Flowers, R. A. I.; Skrydstrup, T. Organic Synthesis Using Samarium Diiodide: A Practical Guide, RSC Publishing, Cambridge, 2010,Chapter 4.
[4]	(a) Namy, J. L.; Girard, P.; Kagan, H. B. Nouv. J. Chim. 1977, 1,5.
	(b) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102,2693.
[5]	(a) Skrydstrup, T. Angew. Chem. In. Ed. 1997, 109,355.
	(b) Krief, A.; Laval, A. M. Chem. Rev. 1999, 99,745.
	(c) Kagan, B. H. Tetrahedron 2003, 59,10351.
	(d) Berndt, M.; Gross, S.; Hlemann, A. Synlett 2004,422.
	(e) Edmonds, D. J.; Johnston, D.; Procter, D. J. Chem. Rev. 2004, 104,3371.
	(f) Jung, D. Y.; Kim, Y. H. Synlett 2005,3019.
	(g) Rudkin, I. M.: Miller, L. C.; Procter, D. J. Organomet. Chem. 2008, 34,19.
	(h) Concellón, J. M.; Rodríguez-Solla, H.; Concellón, C. Chem. Soc. Rev. 2010, 39,4103.
	(i) Gopalaiah, K.; Kagan, H. B. Chem. Rec. 2013, 13,187.
	(j) Gong, H. J.; Jia, X. S.; Zhai, H. B. Chin. J. Org. Chem. 2010, 30,939(in Chinese).
	(巩洪举, 贾学顺, 翟宏斌, 有机化学, 2010, 30,939.)
[6]	Szostak, M.; Fazakerley, N. J.; Parmar, D.; Procter, D. J. Chem. Rev. 2014, 114,5959.
[7]	(a) Edmonds, D. J.; Johnston, D.; Procter, D. J. Chem. Rev. 2004, 104,3371.
	(b) Steel, P. G. J. Chem. Soc., erkin Trans. 1 2001,2727.
	(c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96,307.
	(d) Choppin, S.; Ferreiro-Medeiros, L.; Barbarotto, M. Chem. Soc. Rev. 2013, 42,937.
[8]	Liu, Y. J.; Zhang, Y. M. Acta Chim. Sinica 2005, 63,341(in Chinese).
	(刘永军, 张永敏, 化学学报, 2005, 63,341.)
[9]	Fukuzawa, S.; Nakanishi, A.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commun. 1986,624.
[10]	Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27,5763.
[11]	Koshimizu, M.; Nagatomo, M.; Inoue, M. Tetrahedron 2018: 74 3384.
[12]	Huang, H.-M.; He, Q.; Procter, D. J. Synlett 2020, 31,45.
[13]	Takahashi, K.; Fukushima, K.; Seto, M.; Togashi, A.; Arai, Y.; Honda, T. J. Org. Chem. 2018, 83,10636.
[14]	Fukaya, K.; Tanaka, Y.; Sato, A. C.; Kodama, K.; Yamazaki, H.; Ishimoto, T.; Nozaki, Y.; Iwaki, Y.; Yuki, Y.; Chida, N. Org. Lett. 2015, 17,2570.
[15]	Masson, G.; Py, S.; Vallée, Y. Angew. Chem. Int. Ed. 2002, 41,1772.
[16]	Burchak, O. N.; Py, S. Tetrahedron 2009, 65,7333.
[17]	Gour, J.; Gatadi, S.; Malasala, S.; Yaddanpudi, M. V.; Nanduri, S. J. Org. Chem. 2019, 84,7488.
[18]	Shi, S.-C.; Szostak, M. Org. Lett. 2015, 17,5144.
[19]	Xie, T.-T.; Zhou, L.-J.; Shen, M.-M.; Li, J.-Y.; Lv, X. Tetrahedron Lett. 2015, 56,3982.
[20]	Huang, F.; Zhang, S. L. Org. Lett. 2019, 21,7430.
[21]	Gonzalez-Rodríguez, J.; Soto, M.; Soengas, R. G.; Rodriguezsolla, H. Tetrahedron 2020, 76,130839.
[22]	Doler, C.; Friess, M.; Lackner, F.; Weber, H.; Fischer, R. C.; Breinbauer, R. Tetrahedron 2020, 76,131249.
[23]	Suzuki, K.; Iwasaki, H.; Domasu, R.; Hitotsuyanagi, N.; Wakizaka, Y.; Tominaga, M.; Yamashita, M. Tetrahedron 2015, 71.5513.
[24]	Evdokimovaaa, N. M.; Lamoral-Theys, D.; Mathieu, V. B. Med. Chem. 2011, 19,7252.
[25]	Rossi, A.; Kapahi, P.; Natoli, G. Nature 2000, 403,103.
[26]	(a) Takahashi, K.; Arai, Y.; Honda, T. Tetrahedron Lett. 2017, 58,4048.
	(b) Takahashi, K.; Arai, Y.; Ikegami-Kawai, M.; Honda, T. Tetrahedron 2020, 76,131148.
[27]	Cho, J. Y.; Williams, P. G.; Kwon, H. C.; Jensen, P. R.; Fenical, W. J. Nat. Prod. 2007, 70,1321.
[28]	Takahashi, K.; Fukushima, K.; Tsubuki, M. Tetrahedron Lett. 2018, 59,1435.
[29]	Suzuki, J.; Miyano, N.; Yashiro, S. P.; Umezawa, T. Org. Biomol. Chem. 2017, 15,6557.
[30]	Murakami, S.; Takemoto, T.; Shimizu, Z. Pharm. J. Soc. Jpn. 1953, 73,1026.
[31]	Johnson, R. L.; Koerner, J. F. J. Med. Chem. 1988, 31,2057;.
[32]	Sagrera, G.; Bertucci, A.; Seoane, G. Bioorg. Med. Chem. 2011, 19,3060.
[33]	Soto, M.; Soengas, R. G.; Artur, M. S. Chem.-Eur. J. 2019, 25,13104.
[34]	Liu, X.-J.; Wen, Q.; Xiang, L.; Leng, X.-B.; Chen, Y.-F. Chem.-Eur. J. 2020, 26.5494.
[35]	Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 24,765.
[36]	(a) Miyabe, H.; Toruda, M.; Inoue, K.; Tajiri, K. J. Org. Chem. 1998, 63,4397.
	(b) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116,7447.
[37]	Yoshimura, A.; Saeki, T.; Nomoto, A. Tetrahedron 2015, 71,5347.
[38]	Hassan, A. H. E.; Lee, J. K. .; Pae, A. N.; Min, S.; Cho. Y.-S.. Org. Lett. 2015, 17,2672.
[39]	(a) Li, C. J. Tetrahedron 1996, 52,5643.
	(b) Alonso, F.; Yus, M. Recent Res. Dev. Org. Chem. 1997, 1,39.
	(c) Ramon, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 2,225.
	(d) Kouznetsov, V. V.; Mendez, L. Y. V. Synthesis 2008,491.
[40]	Kagan, H. B.; Namy, J. L. In Lanthanides: Chemistry and Use in Organic Synthesis , Ed.: Kobayashi, S., Springer, New York, 1999, pp.155~198.
[41]	Tomisaka, Y.; Nomoto, A.; Ogawa, A. Tetrahedron Lett. 2009, 50,584.
[42]	Wang, J.; Gasc. F.; Prandi, J. Eur. J. Org. Chem. 2015, 12,2691.
[43]	Aretz, C. D.; Escobedo, H.; Cowen, B. J. Eur. J. Org. Chem. 2018, 16,1880.
[44]	Garduño-Castroa, H. M.; Procter, D. J. Helv. Chim. Acta 2019, 102,e1900227.
[45]	Sinast, M.; Zuccolo, M.; Wischnat, J.; Sube, T.; Baro, A.; Dallavalle, S.; Laschat, S. J. Org. Chem. 2019, 84,10050.
[46]	Chuang, H.; Isobe, M. Tetrahedron 2017, 73,2705.
[47]	Shelby, N. K. C.; Ellery, P.; Chen, S. J. Angew. Chem. Int. Ed. 2009, 48,7140.
[48]	Just-Baringo, X.; Morrill, C.; Procter, D. J. Tetrahedron 2016, 72,7691.
[49]	Mao, H.; You, B.-X.; Zhou, L.-J.; Xie, T.-T.; Wen, Y.-H.; Lv, X.; Wang, X.-X. Org. Biomol. Chem. 2017, 15,6157.
[50]	Marsch, N.; Jones, P-G.; Lindel, T. Beilstein J. Org. Chem. 2015, 11,1700.
[51]	Kern, N.; Plesniak, P. M.; McDouall, J. J. W.; Procter, D. J. Nat. Chem. 2017, 7,1198.
[52]	Nierman, A.; Reissig, H. Synthesis 2020, 52,2721.
[53]	(a) Banik, B. K. Eur. J. Org. Chem. 2002, 15,2431.
	Zeng, Q.; Li, Z.-C.; He, J.-Q. Chin. J. Org. Chem. 2010, 30,345(in Chinese).
	(曾青, 李祖成, 何家骐, 有机化学, 2010, 30,345.)
[54]	(a) Chen, P.; Zhang, D. Tetrahedron 2014, 70,8505.
	(b) Uladzimir, L. ARKIVOC 2014,307.
	(c) Shu, K.; Masaharu, S.; Hidetoshi, K. Chem. Rev. 2002, 102,2227.
[55]	(a) Gao, X.; Wang, X.; Cai, R. F.; Wei, J.-D.; Wu, S.-H. Acta Chim. Sinica 1993, 51,1139(in Chinese).
	(高翔, 王翔, 蔡瑞芳, 卫景德, 吴世晖, 化学学报, 1993, 51,1139.)
	(b) Yu, M.-X.; Zhang, Y.-M. Chem. J. Chin. Univ. 2003, 24,1618(in Chinese).
	(余明新, 张永敏, 高等学校化学学报, 2003, 24,1618.)
	(c) Li, Z. F.; Gao, X.-J.; Lai, G.-Q. J. Organomet. Chem. 2006, 691,4740.
[56]	Liu, Y.-J.; Zhang, D.-M.; Xiao, S.-H. Asian. J. Org. Chem. 2019, 8,858.
[57]	Li, Y.; Deng, P.; Zeng, Y.-M.; Xiong, Y.; Zhou, H. Org. Lett. 2016, 18,1578.
[58]	Liu, Y.-J.; Tian, G.; Li, J.; Qi, Y. J. Org. Chem. 2017, 82,5932.
[59]	Liu, Y.-J.; Xiao. S.-H.; Qi, Y.; Du, F. Chem. Asian J. 2017, 12,673.
[60]	Wang, X.-X.; Li, J.-Y.; Yuan, T.; Xie, G.-Q.; Lv, X. J. Org. Chem. 2018, 83,8984.
[61]	Li, J.-Y.; Niu, Q. -.; Li, S.-H.; Zhou, Q.; Lv, X.; Wang, X.-X. Tetrahedron Lett. 2017, 58,1250.
[62]	You, B. X.; Shen, M.-M.; Xie, G.-Q.; Mao, H.; Lv, X.; Wang, X.-X. Org. Lett. 2018, 20,530.
[63]	Esumi, N.; Nishimoto, Y.; Yasuda, M. Chem.-Eur. J. 2017,2831.
[64]	Wang, Y.-C.; Li, J.-L.; He, Y.; Xie, Y.-Y.; Wang, H.-S.; Pan, Y.-M. Adv. Synth. Catal. 2015, 357,3229.
[65]	Rakhimova, E.-B.; Ismagilov, R.; Zainullin. R. A.; Khalilov, L.; Ibragimov, A.; Dzhemilev, U. Tetrahedron 2016, 72,8223.
[66]	Yu, S.-M.; Cui, K.; Lv, F.; Yang, Z.-Y.; Yao, Z.-J. Tetrahedron Lett. 2016, 57,2818.
[67]	Liu, Y.-J.; Zhao, H.-M.; Tian, G. RSC Adv. 2016, 6,26317.
[68]	Anthore-Dalion, L.; Benischke, A.D; Wei, B. S.; Berionni, G.; Knochel, P. Angew. Chem. Int. Ed. 2019, 58,4046.
[69]	Thurow, S.; Lenardão, E. J.; Just-Baringo, X.; Procter, D. J. Org. Lett. 2017, 19,50.
[70]	Kolmar, S.; Mayer, J. M. J. Am. Chem. Soc. 2017, 139,10687.
[71]	Stockdale, T. F.; Leitch. M. A.; O'Neil, G. W. Synthesis 2020, 52,1544.
[72]	Yokoyama, Y.; Oyamada, S.; Suzuki, J.; Maruyama, S.; Sakusabe, T.; Suzuki, S. Synth. Commun. 2018, 48,1025.

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