Journal of the American Chemical Society
Communication
Ullmann’s Encyclopedia of Industrial Chemistry; Wiley-VCH Verlag
GmbH & Co. KGaA: Weinheim, Germany, 2014; pp 1−18.
(2) For selected reviews, see: (a) Sakakura, T.; Choi, J.-C.; Yasuda,
H. Chem. Rev. 2007, 107, 2365. (b) Omae, I. Coord. Chem. Rev. 2012,
256, 1384. (c) Yeung, C. S.; Dong, V. M. Top. Catal. 2014, 57, 1342.
(d) Liu, Q.; Wu, L.; Jackstell, R.; Beller, M. Nat. Commun. 2015, 6,
5933.
discussions on mechanisms of electrochemical carboxylation of
styrene, see: (a) Gambino, S.; Gennaro, A.; Filardo, G.; Silvestri, G.;
Vianello, E. J. Electrochem. Soc. 1987, 134, 2172. (b) Matthessen, R.;
Fransaer, J.; Binnemans, K.; De Vos, D. E. Beilstein J. Org. Chem. 2014,
10, 2484.
(15) Sim, B. A.; Milne, P. H.; Griller, D.; Wayner, D. D. M. J. Am.
Chem. Soc. 1990, 112, 6635.
(16) (a) Wilger, D. J.; Gesmundo, N. J.; Nicewicz, D. A. Chem. Sci.
(3) For olefins, see: (a) Hoberg, H.; Peres, Y.; Kruger, C.; Tsay, Y.-H.
̈
2013, 4, 3160. (b) Straathof, N. J. W.; Cramer, S. E.; Hessel, V.; Noel,
̈
Angew. Chem., Int. Ed. Engl. 1987, 26, 771. (b) Hendriksen, C.; Pidko,
T. Angew. Chem., Int. Ed. 2016, 55, 15549.
E. A.; Yang, G.; Schaffner, B.; Vogt, D. Chem. - Eur. J. 2014, 20, 12037.
̈
(c) Ostapowicz, T. G.; Schmitz, M.; Krystof, M.; Klankermayer, J.;
Leitner, W. Angew. Chem., Int. Ed. 2013, 52, 12119. (d) Huguet, N.;
Jevtovikj, I.; Gordillo, A.; Lejkowski, M. L.; Lindner, R.; Bru, M.;
Khalimon, A. Y.; Rominger, F.; Schunk, S. A.; Hofmann, P.; Limbach,
M. Chem. - Eur. J. 2014, 20, 16858. (e) Michigami, K.; Mita, T.; Sato,
Y. J. Am. Chem. Soc. 2017, 139, 6094. (f) Gaydou, M.; Moragas, T.;
́ ́
Julia-Hernandez, F.; Martin, R. J. Am. Chem. Soc. 2017, 139, 12161.
For allenes, see: (g) Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2008,
130, 15254. For dienes, see: (h) Bringmann, J.; Dinjus, E. Appl.
Organomet. Chem. 2001, 15, 135. (i) Takimoto, M.; Mori, M. J. Am.
Chem. Soc. 2001, 123, 2895. (j) Takimoto, M.; Nakamura, Y.; Kimura,
K.; Mori, M. J. Am. Chem. Soc. 2004, 126, 5956. For alkynes, see:
(k) Derien, S.; Dunach, E.; Perichon, J. J. Am. Chem. Soc. 1991, 113,
8447. (l) Fujihara, T.; Xu, T.; Semba, K.; Terao, J.; Tsuji, Y. Angew.
Chem., Int. Ed. 2011, 50, 523. (m) Li, S.; Yuan, W.; Ma, S. Angew.
Chem., Int. Ed. 2011, 50, 2578. (n) Wang, X.; Nakajima, M.; Martin, R.
J. Am. Chem. Soc. 2015, 137, 8924.
(4) Direct α-hydrocarboxylation: (a) Williams, C. M.; Johnson, J. B.;
Rovis, T. J. Am. Chem. Soc. 2008, 130, 14936. (b) Greenhalgh, M. D.;
Thomas, S. P. J. Am. Chem. Soc. 2012, 134, 11900. (c) Shao, P.; Wang,
S.; Chen, C.; Xi, C. Org. Lett. 2016, 18, 2050. (d) Kawashima, S.;
Aikawa, K.; Mikami, K. Eur. J. Org. Chem. 2016, 2016, 3166. Direct β-
hydrocarboxylation with stoichiometric metals: (e) Tanaka, S.;
Tanaka, Y.; Chiba, M.; Hattori, T. Tetrahedron Lett. 2015, 56, 3830.
(5) α-Hydrocarboxylation of a limited scope of styrenes using dual
catalytic system involving rhodium and photoredox catalysts was
recently published. See: (a) Murata, K.; Numasawa, N.; Shimomaki,
K.; Takaya, J.; Iwasawa, N. Chem. Commun. 2017, 53, 3098.
Dicarbofunctionalization of styrenes with CO2 and radical precursors
via photoredox catalysis was recently reported. See: (b) Yatham, V. R.;
Shen, Y.; Martin, R. Angew. Chem., Int. Ed. 2017, 56, 10915.
(6) For selected reviews, see: (a) Schultz, D. M.; Yoon, T. P. Science
2014, 343, 1239176. (b) Shaw, M. H.; Twilton, J.; MacMillan, D. W.
C. J. Org. Chem. 2016, 81, 6898. (c) Romero, N. A.; Nicewicz, D. A.
Chem. Rev. 2016, 116, 10075. (d) Douglas, J. J.; Sevrin, M. J.;
Stephenson, C. R. J. Org. Process Res. Dev. 2016, 20, 1134.
(7) Matsuoka, S.; Kohzuki, T.; Pac, C.; Ishida, A.; Takamuku, S.;
Kusaba, M.; Nakashima, N.; Yanagida, S. J. Phys. Chem. 1992, 96, 4437.
(8) Seo, H.; Katcher, M. H.; Jamison, T. F. Nat. Chem. 2017, 9, 453.
(9) Telmesani, R.; Park, S. H.; Lynch-Colameta, T.; Beeler, A. B.
Angew. Chem., Int. Ed. 2015, 54, 11521.
(10) For selected reviews, see: (a) Mallia, C. J.; Baxendale, I. R. Org.
Process Res. Dev. 2016, 20, 327. (b) Cambie,
́
D.; Bottecchia, C.;
Straathof, N. J. W.; Hessel, V.; Noel, T. Chem. Rev. 2016, 116, 10276.
̈
(11) Filardo, G.; Gambino, S.; Silvestri, G.; Gennaro, A.; Vianello, E.
J. Electroanal. Chem. Interfacial Electrochem. 1984, 177, 303.
(12) Lamy, E.; Nadjo, L.; Saveant, J. M. J. Electroanal. Chem.
Interfacial Electrochem. 1977, 78, 403.
(13) The observance of the reduced byproducts of substrates 1g and
4c under the standard conditions (i.e., 4-ethyl-2-methoxyphenol in
28% and 1,1-diphenylethane in 20%, respectively) suggests an
alternative mechanistic pathway for such substrates with extended
conjugation; reduction of styrene to the radical anion and its
nucleophilic addition to CO2. This pathway would provide the same
products and selectivity.
(14) Although the experimental observations are consistent with a
mechanism that proceeds through the initial formation of CO2 radical
anion, we cannot rule out the possibility of involving a styrene radical
anion and homogeneous charge transfer to CO2 at this time. For
D
J. Am. Chem. Soc. XXXX, XXX, XXX−XXX