10.1002/adsc.201801173
Advanced Synthesis & Catalysis
In conclusion, an electrochemical dimethoxylation
M. Dong, J. Am. Chem. Soc. 2008, 130, 2962-2964; c)
J. Seayad, A. M. Seayad, C. L. L. Chai, Org. Lett. 2010,
12, 1412-1415; d) B. C. Giglio, V. A. Schmidt, E. J.
Alexanian, J. Am. Chem. Soc. 2011, 133, 13320-13322;
e) W. Zhong, S. Liu, J. Yang, X. Meng, Z. Li, Org. Lett.
2012, 14, 3336-3339; f) S. Picon, M. Rawling, M.
Campbell, N. C. O. Tomkinson, Org. Lett. 2012, 14,
6250-6253; g) Z. K. Wickens, P. E. Guzmán, Robert H.
Grubbs, Angew. Chem. Int. Ed. 2015, 54, 236-240; h)
Y.-B. Kang, X.-M. Chen, C.-Z. Yao, X.-S. Ning, Chem.
Commun. 2016, 52, 6193-6196; i) B. Yang, Z. Lu,
Chem. Commun. 2017, 53, 12634-12637.
of olefins is unveiled, which is compatible with a
wide range of alkenes. In this efficient transformation,
an ionic-like pathway involves in the reaction, which
provides a complementary method compared with the
radical pathway. More importantly, the two types of
products can be obtained depending on the
substitution pattern of alkenes.
[3] C. J. R. Bataille, T. J. Donohoe, Chem. Soc. Rev. 2011,
40, 114-128.
[4] M. J. Rawling, N. C. O. Tomkinson, Org. Biomol.
Chem. 2013, 11, 1434-1440.
[5] Recent reviews on organic electrosynthesis, see: a) R.;
Francke, R. D. Little, Chem. Soc. Rev. 2014, 43, 2492-
2521; b) M. Yan, Y. Kawamata, P. S. Baran, Chem.
Rev. 2017, 117, 13230-13319; c) J.-i. Yoshida, A.
Shimizu, R. Hayashi, Chem. Rev. 2018, 118, 4702-
4730; d) Y.-Y. Jiang, K. Xu, C.-C. Zeng, Chem. Rev.
2018, 118, 4485-4540; e) Y. Okada, K. Chiba, Chem.
Rev. 2018, 118, 4592-4630; f) S. R. Waldvogel, S. Lips,
M. Selt, B. Riehl, C. J. Kampf, Chem. Rev. 2018, 118,
6706-6765; g) S. Tang, Y.-C. Liu, A.-W. Lei, Chem.
2018, 4, 27-45; h) K. D. Moeller, Chem. Rev. 2018, 118,
4817-4833; i) C. Ma, P. Fang, T.-S. Mei, ACS Catal.
2018, 8, 7179-7189; j) N. Sauermann, T.k H. Meyer, Y.
Qiu, L. Ackermann, ACS Catal. 2018, 8, 7086-7103. k)
S. Liang, K. Xu, C.-C. Zeng, H.-Y. Tian, B.-G. Sun,
Adv. Syn. Catal. DOI: 10.1002/adsc.201800519; Recent
examples, see: l) Z.-W. Hou, Z.-Y. Mao, Y. Y.
Melcamu, X. Lu, H.-C. Xu, Angew. Chem. 2018, 130,
1652-1655; Angew. Chem. Int. Ed. 2018, 57, 1636-
1639;
Scheme 5. Proposed mechanism
Experimental Section
Electrochemical dimethoxylation of olefins (1a as
example):An undivided cell was equipped with a magnet
stirrer, platinum plate (1.5×1.5 cm2) electrode, as the
working electrode and counter electrode. The substrate 1,1-
diphenylethylene 1a (90 mg, 0.5 mmol) and electrolyte n-
Bu4NBF4 (263 mg, 0.8 mmol) was added to the anhydrous
solvent CH3CN/MeOH (7/1 mL) under argon atmosphere.
The resulting mixture was allowed to stir and electrolyze at
constant current conditions (J = 8.9 mA/cm2) at 60 ºC for 2
hours. Then the solvent was removed with a rotary
evaporator and the residue was purified by column
chromatography (EA/PE = 1/50-1/30) on silica gel to
afford the desired product (1,2-dimethoxyethane-1,1-
diyl)dibenzene 2a with 80 % yield.
[6] a) S. Zhang, L.-J. Li, H.-Q. Wang, Q. Li, W.-M. Liu, K.
Xu, C.-C. Zeng, Org. Lett. 2018, 20, 252-255; b) H.-Q.
Wang, J.-J. Zhang, J.-J. Tan, L.-L. Xin, Y.-P. Li, S.
Zhang, K. Xu, Org. Lett. 2018, 20, 2505-2508; c) S.
Zhang, L.-J. Li, M.-Y. Xue, R.-K. Zhang, K. Xu, C.-C.
Zeng, Org. Lett. 2018, 20, 3443-3446.
Acknowledgements
We are grateful to the Natural Science Foundation of China
(21702113, 21602119, U1504208), the financial support from
He’nan Provincial Department of Science and Technology
(182102310608) and acknowledged University Natural Science
Research Project of Anhui Province (KJ2016A334).
[7] G. S. Sauer, S. Lin, ACS Catal. 2018, 8, 5175-5187.
[8] a) Y. Yuan, Y.-X. Chen, S. Tang, Z.-L. Huang, A.-W.
Lei, Sci. Adv. 2018, 4, eaat5312; b) Y. Wang, L.-L.
Deng, H.-B. Mei, B.-N. Du, J.-L. Han, Y. Pan, Green
Chem. 2018, 20, 3444-3449.
References
[9] C.-Y. Cai, H.-C. Xu, Nat. Commun. 2018, 9, 3551.
[10] J. C. Siu, G. S. Sauer, A. Saha, R. L. Macey, N.-K. Fu,
T. Chauvirie, K. L. Lancaster, S. Lin, J. Am. Chem. Soc.
2018, 140, 12511-12520
[1] a) E. N. Jacobsen, I. Marko, W. S. Mungall, G.
Schroeder, K. B. Sharpless, J. Am. Chem. Soc. 1988,
110, 1968-1970; b) H. C. Kolb, M. S. VanNieuwenhze,
K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; c) R.
Bag, P. B. De, S. Pradhan, T. Punniyamurthy, Eur. J.
Org. Chem. 2017, 5424-5438.
[11] Early exploration on electrochemical dimethoxylation:
a) T. Inoue, K. Koyama, T. Matauoka, K. Matsuoka, S.
Tsutsumi, Tetrahedron Lett. 1963, 4, 1409-1411; b) T.
Inoue, K. Koyama, T. Matauoka, K. Matsuoka, S.
Tsutsumi, B. Chem. Soc. Jpn. 1967, 40, 162-168; c) B.
Belleau, Y. K. Au-Young, Can. J. Chem. 1969, 47,
[2] Selected examples: a) Y. Usui, K. Sato, M. Tanaka,
Angew. Chem. 2003, 115, 5781-5783; Angew. Chem.
Int. Ed. 2003, 42, 5623-5625; b) Y. Li, D.-T. Song, V.
4
This article is protected by copyright. All rights reserved.