Citation: Liangliang Qi, Xiaobo Pang, Kai Yin, Qiu-Quan Pan, Xiao-Xue Wei, Xing-Zhong Shu. Mn-mediated reductive C(sp³)–Si coupling of activated secondary alkyl bromides with chlorosilanes[J]. Chinese Chemical Letters, ;2022, 33(12): 5061-5064. doi: 10.1016/j.cclet.2022.03.070 shu

Mn-mediated reductive C(sp³)–Si coupling of activated secondary alkyl bromides with chlorosilanes

Liangliang Qi ^a ,
Xiaobo Pang ^a ,
Kai Yin ^{b, c} ,
Qiu-Quan Pan ^a ,
Xiao-Xue Wei ^a ,
Xing-Zhong Shu ^{a, *,}

a.
State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China
b.
School of Chemistry and Chemical Engineering, Southeast University, Jiangsu Optoelectronic Functional Materials and Engineering Laboratory, Nanjing 211189, China
c.
Zhejiang Nanjiao Chemistry Co., Ltd., Shangyu Economic and Technological Development Zone, Shangyu 312369, China

shuxingzh@lzu.edu.cn

Received Date: 24 January 2022
Revised Date: 9 March 2022
Accepted Date: 16 March 2022
Available Online: 18 March 2022

Figures(6)

The construction of secondary alkylsilanes is a challenging subject in the synthetic community. The cross-coupling provides a practical solution to address this problem, but it typically relies on organometallic species. Herein, we report an Mn-mediated reductive C(sp³)–Si coupling to synthesize these compounds from alkyl and silyl electrophiles. This approach avoids the requirement for activation of Si–Cl by transition metals and thus allows for the coupling of various common chlorosilanes. The reaction proceeds under mild conditions and shows good functional group compatibility. The method offers access to α-silylated organophosphorus and sulfones with a scope that is complementary to those obtained from the established methods.
- Organosilanes,
- Alkylsilanes,
- Reductive coupling,
- Chlorosilanes,
- Organophosphorus,
- Sulfones
1. [1]
  T. Hiyama, Organosilicon compounds in cross-coupling Reactions tamejiro hiyama, in: F. Diederich, P.J. Stang (Eds.), Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, New York, 1998, pp. 421–454.
2. [2]
  T. Hiyama, M. Oestreich, Organosilicon Chemistry: Novel Approaches and Reactions, Wiley-VCH, Weinheim, 2019.
3. [3]
  B. Boutevin, F. Guida-Pietrasanta, A. Ratsimihety, Silicon containing polymers, in: R.G. Jones, W. Ando, J. Chojnowski (Eds.), The Science and Technology of Their Synthesis and Application, Springer, Dordrecht, 2000, pp. 79–112.
4. [4]
  R. Tacke, S. Dorrich, Drug design based on the carbon/silicon switch strategy, in: J. Schwarz (Ed.), Atypical Elements in Drug Design, Springer, Cham, 2016, pp. 29–59.
5. [5]
  B.A. Keay, I. Fleming, Arylsilanes Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, 4, Georg Thieme Verlag, 2002, pp. 685–712.
6. [6]
  B. Marciniec, Hydrosilylation: A Comprehensive Review on Recent Advances, Springer, Dordrecht, 2008.
7. [7]
  D. Troegel, J. Stohrer, Coord. Chem. Rev. 255 (2011) 1440–1459. doi: 10.1016/j.ccr.2010.12.025
8. [8]
  X. Du, Z. Huang, ACS Catal. 7 (2017) 1227–1243. doi: 10.1021/acscatal.6b02990
9. [9]
  J. Chen, J. Guo, Z. Lu, Chin. J. Chem. 36 (2018) 1075–1109. doi: 10.1002/cjoc.201800314
10. [10]
  K. Li, M. Nie, W. Tang, Green Synth. Catal. 1 (2020) 171–174. doi: 10.1016/j.gresc.2020.08.003
11. [11]
  S. Mallick, E.U. Wurthwein, A. Studer, Org. Lett. 22 (2020) 6568–6572. doi: 10.1021/acs.orglett.0c02337
12. [12]
  X. Du, Y. Zhang, D. Peng, Z. Huang, Angew. Chem. Int. Ed. 55 (2016) 6671–6675. doi: 10.1002/anie.201601197
13. [13]
  M.W. Gribble, M.T. Pirnot, J.S. Bandar, R.Y. Liu, S.L. Buchwald, J. Am. Chem. Soc. 139 (2017) 2192–2195. doi: 10.1021/jacs.6b13029
14. [14]
  C. Wang, W.J. Teo, S. Ge, ACS Catal. 7 (2017) 855–863. doi: 10.1021/acscatal.6b02518
15. [15]
  B. Cheng, P. Lu, H. Zhang, X. Cheng, Z. Lu, J. Am. Chem. Soc. 139 (2017) 9439–9442. doi: 10.1021/jacs.7b04137
16. [16]
  M.Y. Hu, Q. He, S.J. Fan, et al., Nat. Commun. 9 (2018) 221–231. doi: 10.1038/s41467-017-02472-6
17. [17]
  S. Bahr, W. Xue, M. Oestreich, ACS Catal. 9 (2019) 16–24. doi: 10.1021/acscatal.8b04230
18. [18]
  K. Murakami, K. Hirano, H. Yorimitsu, K. Oshima, Angew. Chem. Int. Ed. 47 (2008) 5833–5835. doi: 10.1002/anie.200801949
19. [19]
  M. Tobisu, Y. Kita, N. Chatani, J. Am. Chem. Soc. 128 (2006) 8152–8153. doi: 10.1021/ja062745w
20. [20]
  V. Murugesan, V. Balakrishnan, R. Rasappan, J. Catal. 377 (2019) 293–298. doi: 10.1016/j.jcat.2019.07.026
21. [21]
  Y.Y. Kong, Z.X. Wang, Adv. Synth. Catal. 361 (2019) 5440–5448. doi: 10.1002/adsc.201900949
22. [22]
  K.M. Korch, D.A. Watson, Chem. Rev. 119 (2019) 8192–8228. doi: 10.1021/acs.chemrev.8b00628
23. [23]
  J. Terao, K. Torii, K. Saito, et al., Angew. Chem. Int. Ed. 37 (1998) 2653–2656. doi: 10.1002/(SICI)1521-3773(19981016)37:19<2653::AID-ANIE2653>3.0.CO;2-3
24. [24]
  J.R. McAtee, S.E.S. Martin, D.T. Ahneman, K.A. Johnson, D.A. Watson, Angew. Chem. Int. Ed. 51 (2012) 3663–3667. doi: 10.1002/anie.201200060
25. [25]
  S.E.S. Martin, D.A. Watson, J. Am. Chem. Soc. 135 (2013) 13330–13333. doi: 10.1021/ja407748z
26. [26]
  C.K. Chu, Y. Liang, G.C. Fu, J. Am. Chem. Soc. 138 (2016) 6404–6407. doi: 10.1021/jacs.6b03465
27. [27]
  W. Xue, Z.W. Qu, S. Grimme, M. Oestreich, J. Am. Chem. Soc. 138 (2016) 14222–14225. doi: 10.1021/jacs.6b09596
28. [28]
  W. Xue, M. Oestreich, Angew. Chem. Int. Ed. 56 (2017) 11649–11652. doi: 10.1002/anie.201706611
29. [29]
  J. Scharfbier, H. Hazrati, E. Irran, M. Oestreich, Org. Lett. 19 (2017) 6562–6565. doi: 10.1021/acs.orglett.7b03279
30. [30]
  W. Xue, R. Shishido, M. Oestreich, Angew. Chem. Int. Ed. 57 (2018) 12141–12145. doi: 10.1002/anie.201807640
31. [31]
  J. Scharfbier, B.M. Gross, M. Oestreich, Angew. Chem. Int. Ed. 59 (2020) 1577–1580. doi: 10.1002/anie.201912490
32. [32]
  S. Wang, M. Sun, H. Zhang, et al., CCS Chem. 3 (2021) 2164–2173. doi: 10.31635/ccschem.020.202000447
33. [33]
  V. Balakrishnan, V. Murugesan, B. Chindan, R. Rasappan, Org. Lett. 23 (2021) 1333–1338. doi: 10.1021/acs.orglett.0c04316
34. [34]
  A.P. Cinderella, B. Vulovic, D.A. Watson, J. Am. Chem. Soc. 139 (2017) 7741–7744. doi: 10.1021/jacs.7b04364
35. [35]
  B. Vulovic, A.P. Cinderella, D.A. Watson, ACS Catal. 7 (2017) 8113–8117. doi: 10.1021/acscatal.7b03465
36. [36]
  C.E.I. Knappke, S. Grupe, D. Gärtner, et al., Chem. Eur. J. 20 (2014) 6828–6942. doi: 10.1002/chem.201402302
37. [37]
  T. Moragas, A. Correa, R. Martin, Chem. Eur. J. 20 (2014) 8242–8258. doi: 10.1002/chem.201402509
38. [38]
  E.L. Lucas, E.R. Jarvo, Nat. Rev. Chem. 1 (2017) 0065–0071. doi: 10.1038/s41570-017-0065
39. [39]
  M.J. Goldfogel, L. Huang, D.J. Weix, Cross electrophile coupling: principles and new reactions, in: S. Ogoshi (Ed.), Nickel Catalysis in Synthesis: Methods and Reactions, Wiley-VCH, Weinheim, 2020, pp. 183–222.
40. [40]
  J. Liu, Y. Ye, J.L. Sessler, H. Gong, ACC Chem. Res. 53 (2020) 1833–1845. doi: 10.1021/acs.accounts.0c00291
41. [41]
  K.E. Poremba, S.E. Dibrell, S.E. Reisman, ACS Catal. 10 (2020) 8237–8246. doi: 10.1021/acscatal.0c01842
42. [42]
  X. Pang, X. Peng, X.Z. Shu, Synthesis (Mass) 52 (2020) 3751–3763. doi: 10.1055/s-0040-1707342
43. [43]
  P. Zheng, P. Zhou, D. Wang, et al., Nat. Commun. 12 (2021) 1646. doi: 10.1038/s41467-021-21947-1
44. [44]
  D. Wang, T. Xu, ACS Catal. 11 (2021) 12469–12475. doi: 10.1021/acscatal.1c03265
45. [45]
  X.G. Jia, P. Guo, J. Duan, X.Z. Shu, Chem. Sci. 9 (2018) 640–645. doi: 10.1039/C7SC03140H
46. [46]
  X.B. Yan, C.L. Li, W.J. Jin, P. Guo, X.Z. Shu, Chem. Sci. 9 (2018) 4529–4534. doi: 10.1039/C8SC00609A
47. [47]
  R.D. He, C.L. Li, Q.Q. Pan, et al., J. Am. Chem. Soc. 141 (2019) 12481–12486. doi: 10.1021/jacs.9b05224
48. [48]
  H. Xie, J. Guo, Y.Q. Wang, et al., J. Am. Chem. Soc. 142 (2020) 16787–16794. doi: 10.1021/jacs.0c07492
49. [49]
  P. Guo, K. Wang, W.J. Jin, et al., J. Am. Chem. Soc. 143 (2021) 513–523. doi: 10.1021/jacs.0c12462
50. [50]
  P.F. Su, K. Wang, X. Peng, et al., Angew. Chem. Int. Ed. 60 (2021) 26571–26576. doi: 10.1002/anie.202112876
51. [51]
  J. Duan, K. Wang, G.L. Xu, et al., Angew. Chem. Int. Ed. 59 (2020) 23083–23088. doi: 10.1002/anie.202010737
52. [52]
  L. Zhang, M. Oestreich, Angew. Chem. Int. Ed. 60 (2021) 18587–1859. doi: 10.1002/anie.202107492
53. [53]
  M. Xing, H. Cui, C. Zhang, Org. Lett. 23 (2021) 7645–7649. doi: 10.1021/acs.orglett.1c02887
54. [54]
  J. Duan, Y. Wang, L. Qi, et al., Org. Lett. 23 (2021) 7855–7859. doi: 10.1021/acs.orglett.1c02874
55. [55]
  H. Yamashita, M. Tanaka, M. Goto, Organometallics 16 (1997) 4696–4707. doi: 10.1021/om970214y
56. [56]
  B. Vulovic, A.P. Cinderella, D.A. Watson, ACS Catal. 7 (2017) 8113–8117. doi: 10.1021/acscatal.7b03465
57. [57]
  K. Matsumoto, J. Huang, Y. Naganawa, et al., Org. Lett. 20 (2018) 2481–2484. doi: 10.1021/acs.orglett.8b00847
58. [58]
  D.J. Ager, The peterson olefination reaction, in: L.P. Paquette (Ed.), Organic Reactions, Wiley, 1990, pp. 1–219.
59. [59]
  P.S. Jones, S.V. Ley, N.S. Simpkins, A.J. Whittle, Tetrahedron 42 (1986) 6519–6534. doi: 10.1016/S0040-4020(01)88114-X
60. [60]
  M.B. Anderson, P.L. Fuchs, J. Org. Chem. 55 (1990) 337–342. doi: 10.1021/jo00288a058
61. [61]
  D.J. Ager, J. Chem. Soc. Chem. Commun. (1984) 486–488.
62. [62]
  D. Craig, S.V. Ley, N.S. Simpkins, G.H. Whitham, M.J. Prior, J. Chem. Soc. Perkin Trans. 1 (1985) 1949–1952.
63. [63]
  E.E. Aboujaoude, S. Liétjé, N. Collignon, M.P. Teulade, P.A. Savignac, Synthesis 11 (1986) 934–937.
64. [64]
  A.G. Shipov, Y.I. Baukov, Zh. Obshch. Khim. 54 (1984) 1842.
65. [65]
  H. Keipour, V. Carreras, T. Ollevier, Org. Biomol. Chem. 15 (2017) 5441–5456. doi: 10.1039/C7OB00807D
66. [66]
  W. Ando, A. Sekiguchi, T. Hagiwara, et al., J. Am. Chem. Soc. 101 (1979) 6393–6398. doi: 10.1021/ja00515a038
67. [67]
  S.B.J. Kan, R.D. Lewis, K. Chen, F.H. Arnold, Science 354 (2016) 1048–1051. doi: 10.1126/science.aah6219
68. [68]
  D. Chen, D.X. Zhu, M.H. Xu, J. Am. Chem. Soc. 138 (2016) 1498–1501. doi: 10.1021/jacs.5b12960
69. [69]
  W. Tang, X. Zhang, Chem. Rev. 103 (2003) 3029–3070. doi: 10.1021/cr020049i
70. [70]
  P.W.N.M. van Leeuwen, P.C.J. Kamer, C. Claver, O. Pamies, M. Dièguez, Chem. Rev. 111 (2011) 2077–2118. doi: 10.1021/cr1002497
71. [71]
  M. Mellah, A. Voituriez, E. Schulz, Chem. Rev. 107 (2007) 5133–5209. doi: 10.1021/cr068440h
72. [72]
  C. Li, Catal. Rev. 46 (2004) 419–492. doi: 10.1081/CR-200036734
73. [73]
  L. Barfacker, D.E. Tom, P. Eilbraeht, Tetrahedron Lett. 40 (1999) 4031–4034. doi: 10.1016/S0040-4039(99)00678-4
74. [74]
  P.P. Matloka, K.B. Wagener, J. Mol. Catal. A 257 (2006) 89–98. doi: 10.1016/j.molcata.2006.06.006
75. [75]
  J.W. Park, C.H. Jun, J. Am. Chem. Soc. 132 (2010) 7268–7269. doi: 10.1021/ja102741k
76. [76]
  M.I. Antczak, J.L. Montchamp, J. Org. Chem. 74 (2009) 3758–3766. doi: 10.1021/jo900300c
77. [77]
  K. Chang, B. Ku, D.Y. Oh, Syn. Commun. 19 (1989) 1891–1898. doi: 10.1080/00397918908052580
78. [78]
  M. Linnert, C. Bruhn, C. Wagner, D. Steinborn, J. Organomet. Chem. 691 (2006) 2358–2367. doi: 10.1016/j.jorganchem.2005.12.048
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5. [5]
  Hui LIU , Lin XIA , Yun Hua YE . Organophosphorus Compound DEPBT as a Coupling Reagent for Oligopeptides and Peptoids Synthesis:Studies on Its Mechanism. Chinese Chemical Letters, 2002, 13(7): 601-604.
6. [6]
  Yan Nei HE , Yao LIN . Application of an Organophosphorus Compound-DEPBT as Coupling Reagent in Liquid Phase Peptide Synthesis. Chinese Chemical Letters, 1997, 8(9): 749-750.
7. [7]
  Wen Yan Hao , Jian Wen Jiang , Ming Zhong Cai . A facile stereospecific synthesis of (Z)-2-sulfonyl-substituted 1, 3-enynes via Sonogashira coupling of (E)-α-iodovinyl sulfones with 1-alkynes. Chinese Chemical Letters, 2007, 18(7): 773-776. doi: 10.1016/j.cclet.2007.05.021
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  Reza Heydari Malek Taher Maghsoodlou , Razieh Nejat Yami . An efficient method for synthesis of organophosphorus compounds in aqueous media. Chinese Chemical Letters, 2009, 20(10): 1175-1178. doi: 10.1016/j.cclet.2009.05.019
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  Jian Xue , Lu Ling Wu , Xian Huang . The facile insertion of β-keto sulfones to arynes:The direct preparation of polysubstituted ortho-keto benzyl sulfones. Chinese Chemical Letters, 2008, 19(6): 631-633. doi: 10.1016/j.cclet.2008.04.006
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  Chen Zhen , Guo Kang , Chen Rongshun , Gu Chen , Zhou Huating , Zhu Yingguang . Facile Access to β-Ketosulfones via Mn-Mediated Reductive Coupling of α-Bromoketones with Sulfonyl Chlorides. Chinese Journal of Organic Chemistry, 2018, 38(4): 963-968. doi: 10.6023/cjoc201710027
13. [13]
  Ji Ming ZHANG , Yong Min ZHANG . Catalytic HgCl₂-Samarium System Induced Reductive Coupling of Nitriles with Nitro Compounds. Chinese Chemical Letters, 2002, 13(2): 97-100.
14. [14]
  Zhi Fang LI , Ping LU , Yong Min ZHANG . Facile Synthesis of Amidines via Intermolecular Reductive Coupling of Nitriles with Azobenzene Promoted by Samarium Diiodide. Chinese Chemical Letters, 2000, 11(6): 495-498.
15. [15]
  Da Qing SHI , Lai Long MU , Zai Sheng LU , Gui Yuan DAI . Low-valent Titanium Induced Reductive Coupling Reaction of Aryl Sulfonyl Chlorides with α,β-Unsaturated Esters. Chinese Chemical Letters, 1997, 8(8): 677-678.
16. [16]
  Zi Jie HOU , Li dun LIU , Yu Lin LI . LOW-VALENT TITANIUM INDUCED REDUCTIVE COUPLING REACTION OF AROMATIC α-HYDROXY KETONES. Chinese Chemical Letters, 1992, 3(4): 279-280.
17. [17]
  Da Qing SHI , Wei Xing CHEN . LOW-VALENT TITANIUM INDUCED REDUCTIVE CROSS-COUPLING REACTION OF ESTERS WITH DIARYL KETONES. Chinese Chemical Letters, 1993, 4(11): 941-942.
18. [18]
  Wei Xing CHEN , Jian Xie CHEN , Jian Ping JIANG , Tsi Yu KAO . LOW-VALENT TITANIUM INDUCED REDUCTIVE COUPLING OF AROMATIC NTTRILES TO 1,2-ARYLETHANONES. Chinese Chemical Letters, 1991, 2(5): 351-352.
19. [19]
  Wang Shuai , Yang Cheng , Sun Shuo , Sun Hanli , Wang Jianbo . Palladium-Catalyzed Reductive Coupling of Aromatic Bromides and Trimethylsilyldiazomethane: Its Application to Methylation of Aromatic Compounds. Chinese Journal of Organic Chemistry, 2020, 40(11): 3881-3888. doi: 10.6023/cjoc202006075
20. [20]
  Shuo Chen , Qingru Wen , Yanqing Zhu , Yanru Ji , Yu Pu , Zhengli Liu , Yun He , Zhang Feng . Boron-promoted reductive deoxygenation coupling reaction of sulfonyl chlorides for the C(sp³)-S bond construction. Chinese Chemical Letters, 2022, 33(12): 5101-5105. doi: 10.1016/j.cclet.2022.04.022

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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Mn-mediated reductive C(sp3)–Si coupling of activated secondary alkyl bromides with chlorosilanes

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通讯作者: 陈斌, bchen63@163.com

Mn-mediated reductive C(sp³)–Si coupling of activated secondary alkyl bromides with chlorosilanes