Synthesis 2022; 54(11): 2661-2668 DOI: 10.1055/a-1742-2821
Synthesis of Dibenzotetrathiafulvalenes of Oxalic Acid with Electron-Rich Aromatic 1,2-Dithiols and Application to Dithioacetalization with 9-Fluorenecarboxylic Acids or Dicarboxylic Acids
,
Kohei Minato
,
Shota Nakata
,
We thank the Japan Society for the Promotion of Science (JSPS KAKENHI Grant Number JP19K05463). Also, this research was partially supported by the Ogawa Sho research fund.
Abstract
We have developed a two-step synthesis of dibenzotetrathiafulvalene (DBTTF) derivatives by combining the indium-catalyzed reductive dithioacetalization of oxalic acid and electron-rich aromatic dithiols with a subsequent oxidation of the resultant dithioacetals. The same transformation of electron-rich aromatic dithiols with either 9-fluorenecarboxylic acid derivatives or dicarboxylic acids effectively produced the corresponding benzo-1,3-dithiafulvene derivatives.
Key words
dibenzotetrathiafulvalene -
dicarboxylic acids -
dithioacetalization -
hydrosilane -
indium -
reduction -
oxidation
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/a-1742-2821.
Supporting Information
Publication History
Received: 22 December 2021
Accepted after revision: 17 January 2022
Accepted Manuscript online: 17 January 2022
Article published online: 10 March 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, Germany
References
For example:
1a
Yorimitsu H,
Yoshimura A,
Misaki Y.
Synthesis 2020; 52: 3326
1b
Sarhan AE.-W. A. O.
Tetrahedron 2005; 61: 3889
1c
Gorgues A,
Hudhomme P,
Sallé M.
Chem. Rev. 2004; 104: 5151
1d
Bendikov M,
Wudl F,
Perepichka DF.
Chem. Rev. 2004; 104: 4891
1e
Fabre JM.
Chem. Rev. 2004; 104: 5133
1f
Schukat G,
Fanghänel E.
Sulfur Rep. 1996; 18: 1
1g
Moore AJ,
Bryce MR.
Synthesis 1997; 407
1h
Krief A.
Tetrahedron 1986; 42: 1204
1i
Bryce MR.
J. Chem. Soc., Perkin Trans. 1 1985; 1675
1j
Ferraris J,
Cowan DO,
Walatka V,
Perlstein JH.
J. Am. Chem. Soc. 1973; 95: 948
1k
Coleman LB,
Cohen MJ,
Sandman DJ,
Yamagishi FG,
Garito AF,
Heeger AJ.
Solid State Commun. 1973; 12: 1125
1l
Coffen DL,
Chambers JQ,
Williams DR,
Garrett PE,
Canfield ND.
J. Am. Chem. Soc. 1971; 93: 2258 ; see also the references cited therein
2
Nakayama J.
Sulfur Rep. 1985; 4: 159 ; and references cited therein
For example:
3a
Nafe J,
Knochel P.
Synthesis 2016; 48: 103
3b
Ito T,
Nakamura K.-i,
Shirahata T,
Kawamoto T,
Mori T,
Misaki Y.
Chem. Lett. 2011; 40: 81
3c
Hasegawa M,
Takano J.-i,
Enozawa H,
Kuwatani Y,
Iyoda M.
Tetrahedron Lett. 2004; 45: 4109
3d
Imakubo T,
Sawa H,
Kato R.
Synth. Met. 1997; 86: 1883
3e
Garín J,
Orduna J,
Savirón M,
Bryce MR,
Moore AJ,
Morisson V.
Tetrahedron 1996; 52: 11063
3f
Gompper R,
Hock J,
Polborn K,
Dormann E,
Winter H.
Adv. Mater. 1995; 7: 41
3g
Sadekov ID,
Rivkin BB,
Minkin VI.
Sulfur Rep. 1993; 15: 103
3h
Müller H,
Ueba Y.
Bull. Chem. Soc. Jpn. 1993; 66: 1773
3i
Misaki Y,
Nishikawa H,
Nomura K,
Yamabe T,
Yamochi H,
Saito G,
Sato T,
Shiro M.
J. Chem. Soc., Chem. Commun. 1992; 1410
3j
Prinzbach H,
Berger H,
Lüttringhaus A.
Angew. Chem., Int. Ed. Engl. 1965; 4: 435 ; see also the references cited therein
4a
Yamada J.-i,
Amano Y,
Takasaki S,
Nakanishi R,
Matsumoto K,
Satoki S,
Anzai H.
J. Am. Chem. Soc. 1995; 117: 1149
4b
Yamada J.-i,
Nishimoto Y,
Tanaka S,
Nakanishi R,
Hagiya K,
Anzai H.
Tetrahedron Lett. 1995; 36: 9509
5
Melby LR,
Hartzler HD,
Sheppard WA.
J. Org. Chem. 1974; 39: 2456
6a
Nakayama J.
J. Chem. Soc., Chem. Commun. 1974; 166
6b
Nakayama J.
Synthesis 1975; 38
6c
Gimbert Y,
Moradpour A,
Bittner S.
Tetrahedron Lett. 1990; 31: 1007
7a
Nakayama J,
Fujiwara K,
Hoshino M.
Bull. Chem. Soc. Jpn. 1976; 49: 3567
7b
Nakayama J,
Seki E,
Hoshino M.
J. Chem. Soc., Perkin Trans. 1 1978; 468
8
Hurtley WR. H,
Smiles S.
J. Chem. Soc. 1926; 129: 2263
9a
Mizuno M,
Cava MP.
J. Org. Chem. 1978; 43: 416
9b
Bajwa GS,
Berlin KD,
Pohl HA.
J. Org. Chem. 1976; 41: 145
10a
Sakai N,
Miyazaki T,
Sakamoto T,
Yatsuda T,
Moriya T,
Ikeda R,
Konakahara T.
Org. Lett. 2012; 14: 4366
10b
Nishino K,
Minato K,
Miyazaki T,
Ogiwara Y,
Sakai N.
J. Org. Chem. 2017; 82: 3659
11
Schuler E,
Demetriou M,
Shiju NR,
Gruter G.-JM.
ChemSusChem 2021; 14: 3636 ; and references cited therein
12 When dithioacetalization was performed with either 20 mol% of InI3 or a longer reaction time (9 h), the product yield of 1a was not improved.
13 Unlike the reaction with 4,5-dichloro-1,2-benzenedithiol shown in Scheme 2, when the same dithioacetalization was examined with 3,6-dichloro-1,2-benzenedithiol, a related electron-deficient benzenedithiol, the desired product was not obtained, probably because of the low nucleophilicity of these benzenedithiols with an electron-withdrawing group.
14 Formation of 1f was only detected by GC-MS, but the expected dithioacetal was not isolated.
15
Ueno Y,
Nakayama A,
Okawara M.
J. Chem. Soc., Chem. Commun. 1978; 74
For example:
16a
Salami F,
Zhao Y.
New J. Chem. 2020; 44: 9179
16b
Perepichka DF,
Perepichka IF,
Ivasenko O,
Moore AJ,
Bryce MR,
Kuz’mina LG,
Batsanov AS,
Sokolov NI.
Chem. Eur. J. 2008; 14: 2757
16c
Skabara PJ,
Serebryakov IM,
Perepichka IF,
Sariciftci NS,
Neugebauer H,
Cravino A.
Macromolecules 2001; 34: 2232
16d
Mysyk DD,
Perepichka IF,
Perepichka DF,
Bryce MR,
Popov AF,
Goldenberg LM,
Moore AJ.
J. Org. Chem. 1999; 64: 6937
For example:
17a
Akiba K.-y,
Ishikawa K,
Inamoto N.
Bull. Chem. Soc. Jpn. 1978; 51: 2674
17b
Akiba K.-y,
Ishikawa K,
Inamoto N.
Synthesis 1977; 861
18
Moriya T,
Yoneda S,
Kawana K,
Ikeda R,
Konakahara T,
Sakai N.
J. Org. Chem. 2013; 78: 10642
19
Kawase T,
Awaji H,
Yoneda S,
Yoshida Z.-i.
Heterocycles 1982; 18: 12
20
Block E,
Eswarakrishnan V,
Gernon M,
Ofori-Okai G,
Saha C,
Tang K,
Zubieta J.
J. Am. Chem. Soc. 1989; 111: 658
21
Degani I,
Fochi R.
J. Chem. Soc., Perkin Trans. 1 1976; 1886
22
Lindsay CM,
Smith K,
Brown CA,
Betterton-Cruz K.
Tetrahedron Lett. 1984; 25: 995
23
Yoshino T,
Shibata K,
Wada H,
Bando Y,
Ishikawa K,
Takezoe H,
Mori T.
Chem. Lett. 2009; 38: 200
24
Nagakubo J,
Ashizawa M,
Kawamoto T,
Tanioka A,
Mori T.
Phys. Chem. Chem. Phys. 2011; 13: 14370
25 For the related compound without a methyl group of compound 7 , see:
Bryce MR,
Fleckenstein E,
Hünig S.
J. Chem. Soc., Perkin Trans. 1 1990; 1777