One-Shot Deprotonative Metalation/Transmetalation/Polymerization of Halothiophenes Catalyzed by Nickel Complex for Polythiophene Synthesis

Abstract

Effect of divalent metals was studied in the cross-coupling polymerization of thiophenes leading to head-to-tail-type poly-3-hexyl­thiophene. Deprotonation of the C–H bond at the 5-position of 2-halo-3-hexylthiophene by LDA followed by metal exchange was carried out in one pot and following addition of nickel catalyst underwent polymerization. One-shot reaction involving deprotonation/transmetalation/ cross coupling polymerization was also examined with manganese(II) chloride and nickel(II) catalyst.

Key words

deprotonative metalation - poly(3-hexylthiophene) - group II metals - nickel catalyst - one-shot reaction

Publikationsverlauf

Eingereicht: 25. Dezember 2020

Angenommen nach Revision: 21. Januar 2021

Accepted Manuscript online:
21. Januar 2021

Artikel online veröffentlicht:
15. Februar 2021

• References

• 1a Sirringhaus H, Tessler N, Friend RH. Science 1998; 280: 1741
• 1b Cho KY, Kim HJ, Do XH, Seo JY, Hwang SS, Choi DH, Baek KY. Compos. Sci. Technol. 2019; 174: 149
• 1c Osaka I, McCullough RD. Acc. Chem. Res. 2008; 41: 1202
• 1d Bao Z, Dodabalapur A, Lovinger AJ. Appl. Phys. Lett. 1996; 69: 4108
• 2a Okamoto K, Luscombe CK. Polym. Chem. 2011; 2: 2424
• 2b Yokozawa T, Ohta Y. Chem. Rev. 2016; 116: 1950
• 2c Amna B, Siddiqi HM, Hassan A, Ozturk T. RSC Adv. 2020; 10: 4322
• 3a Mori A. J. Synth. Org. Chem. Jpn. 2011; 69: 1202
• 3b Shibuya Y, Mori A. Chem. Eur. J. 2020; 26: 6976
• 3c Mori A. Bull. Chem. Soc. Jpn. 2020; 93: 1200
• 4a Loewe RS, Khersonsky SM, McCullough RD. Adv. Mater. 1999; 11: 250
• 4b Yokoyama A, Miyakoshi R, Yokozawa T. Macromolecules 2004; 37: 1169
• 4c Kiriy A, Senkovskyy V, Sommer M. Macromol. Chem. Rapid Commun. 2011; 32: 1503
• 4d Bronstein HA, Luscombe CK. J. Am. Chem. Soc. 2009; 131: 12894
• 4e Ye S, Foster SM, Pollit AA, Cheng S, Seferos DS. Chem. Sci. 2019; 10: 2075
• 5a Tamba S, Tanaka S, Okubo Y, Meguro H, Okamoto S, Mori A. Chem. Lett. 2011; 40: 398
• 5b Tamba S, Mitsuda S, Tanaka F, Sugie A, Mori A. Organometallics 2012; 31: 2263
• 5c Tamba S, Fuji K, Meguro H, Okamoto S, Tendo T, Komobuchi R, Sugie A, Nishino T, Mori A. Chem. Lett. 2013; 42: 281
• 5d Murakami K, Tanaka S, Mori A. Polym. Chem. 2015; 6: 6573
• 5e Fujita K, Sumino Y, Ide K, Tamba S, Shono K, Shen J, Nishino T, Mori A, Yasuda T. Macromolecules 2016; 49: 1259
• 5f Ogura T, Kubota C, Suzuki T, Okano K, Tanaka N, Matsumoto T, Nishino T, Mori A, Okita T, Funahashi M. Chem. Lett. 2019; 48: 611
• 5g Shibuya Y, Nakagawa N, Miyagawa N, Suzuki T, Okano K, Mori A. Angew. Chem. Int. Ed. 2019; 58: 9547
• 5h Mori A, Kubota C, Fujita K, Hayashi M, Ogura T, Suzuki T, Okano K, Funahashi M, Horie M. Macromolecules 2020; 53: 1171
• 6a Iraqi A, Barker GW. J. Mater. Chem. 1998; 8: 25
• 6b Guillerez S, Bidan G. Synth. Met. 1998; 93: 123
• 6c Wang Q, Takita R, Kikuzaki Y, Ozawa F. J. Am. Chem. Soc. 2010; 132: 11420
• 6d Bonillo B, Swager TM. J. Am. Chem. Soc. 2012; 134: 18916
• 7a Chen TA, Rieke RD. J. Am. Chem. Soc. 1992; 114: 10087
• 7b Chen TA, Wu XM, Rieke RD. J. Am. Chem. Soc. 1995; 117: 233
• 8a McCullough RD, Lowe RD. J. Chem. Soc., Chem. Commun. 1992; 70
• 8b Higashihara T, Goto E, Ueda M. ACS Macro Lett. 2012; 1: 167
• 9a Fuji K, Tamba S, Shono K, Sugie A, Mori A. J. Am. Chem. Soc. 2013; 135: 12208
• 9b Shono K, Sumino Y, Tanaka S, Tamba S, Mori A. Org. Chem. Front. 2014; 1: 678
• 9c Westerhausen M. Coord. Chem. Rev. 2008; 252: 1516
• 10a Frischmuth A, Fernández M, Barl NM, Achrainer F, Zipse H, Berionni G, Mayr H, Karaghiosoff K, Knochel P. Angew. Chem. Int. Ed. 2014; 53: 7928
• 10b Brikci-Nigassa N, Bentabed-Ababsa G, Erb W, Mongin F. Synthesis 2018; 50: 3615
• 11 SEC analysis suggested the formation of a small amount of high-molecular-weight of polymer, which has also been observed in the Murahashi coupling polymerization (ref. 9). See also Supporting Information.
• 12a Tsubogo T, Yamashita Y, Kobayashi S. Chem. Eur. J. 2012; 18: 13624
• 12b Wilson AS. S, Hill MS, Mahon MF, Dinoi C, Maron L. Science 2017; 358: 1168
• 13 Miyoshi N, Kimura S, Kubo S, Ohmura SD, Ueno M. Asian J. Org. Chem. 2020; 9: 1660
• 14 Yanagisawa A, Habaue S, Yasue K, Yamamoto H. J. Am. Chem. Soc. 1994; 116: 6130
• 15a Hojo M, Harada H, Ito H, Hosomi A. J. Am. Chem. Soc. 1997; 119: 5459
• 15b Oshima K. J. Organomet. Chem. 1999; 575: 1
• 15c Concellón JM, Rodríguez-Solla H, Del Amo V. Chem. Eur. J. 2008; 14: 10184
• 15d See also: Rieke R. Patent WO 2007146074 A1, 2007
• 16 Tamba S, Shono K, Sugie A, Mori A. J. Am. Chem. Soc. 2011; 133: 9700
• 17 Hayashi Y. Chem. Sci. 2016; 7: 866
• 18 Inoue R, Yamaguchi M, Murakami Y, Okano K, Mori A. ACS Omega 2018; 3: 12703