Organic Letters
Letter
(11) For Co case, see: (a) Liu, Z.; Yang, Z.; Yu, X.; Zhang, H.; Yu,
B.; Zhao, Y.; Liu, Z. Org. Lett. 2017, 19, 5228−5231. For Fe case, see:
(b) Ma, W.; Cui, S.; Sun, H.; Tang, W.; Xue, D.; Li, C.; Fan, J.; Xiao,
J.; Wang, C. Chem. - Eur. J. 2018, 24, 13118−13123. For Mn cases,
see: (c) Jana, A.; Reddy, C. B.; Maji, B. ACS Catal. 2018, 8, 9226−
9231. (d) Borghs, J. C.; Tran, M. A.; Sklyaruk, J.; Rueping, M.; El-
Sepelgy, O. J. Org. Chem. 2019, 84, 7927−7935. For Ni case, see:
(e) Bera, S.; Bera, A.; Banerjee, D. Chem. Commun. 2020, 56, 6850−
6853. For a recent case with secondary alcohols by a Co catalyst, see:
(f) Chakraborty, P.; Garg, N.; Manoury, E.; Poli, R.; Sundararaju, B.
ACS Catal. 2020, 10, 8023−8031.
acknowledge Clean Energy Fee Funds of Middle Tennessee
State University.
REFERENCES
■
(1) (a) Fleming, F. F. Nat. Prod. Rep. 1999, 16, 597−606.
(b) Fleming, F. F.; Wang, Q. Chem. Rev. 2003, 103, 2035−2078.
(c) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103,
811−892. (d) Boyer, J.; Corriu, R. J. P.; Perz, R.; Reye, C. Tetrahedron
1983, 39, 117−122. (e) Gomez, R.; Segura, J. L.; Martin, N. Chem.
Commun. 1999, 619−620. (f) Segura, J. L.; Martin, N.; Hanack, M.
Eur. J. Org. Chem. 1999, 1999, 643−651. (g) An, M.; Sarker, A. K.;
Jung, D. C.; Hong, J. D. Bull. Korean Chem. Soc. 2011, 32, 2083−
2086.
(12) (a) Xu, S.; Alhthlol, L. M.; Paudel, K.; Reinheimer, E.; Tyer, D.
L.; Taylor, D. K.; Smith, A. M.; Holzmann, J.; Lozano, E.; Ding, K.
Inorg. Chem. 2018, 57, 2394−2397. (b) Paudel, K.; Pandey, B.; Xu, S.;
Taylor, D. K.; Tyer, D. L.; Torres, C. L.; Gallagher, S.; Kong, L.; Ding,
K. Org. Lett. 2018, 20, 4478−4481. (c) Pandey, B.; Xu, S.; Ding, K.
Org. Lett. 2019, 21, 7420−7423. (d) Pandey, B.; Xu, S.; Ding, K.
Organometallics 2021, 40, 1207. (e) Paudel, K.; Xu, S.; Hietsoi, O.;
Pandey, B.; Onuh, C.; Ding, K. Organometallics 2021, 40, 418−426.
(f) Paudel, K.; Xu, S.; Ding, K. J. Org. Chem. 2020, 85, 14980−14988.
(13) For selective cases, see: (a) Walling, C.; Bollyky, L. J. Am.
Chem. Soc. 1964, 86, 3750−3752. (b) Berkessel, A.; Schubert, T. J. S.;
(2) (a) Arseniyadis, S.; Kyler, K. S.; Watt, D. S. Org. React. 1984, 31,
193. (b) DiBiase, S. A.; Lipisko, B. A.; Haag, A.; Wolak, A. R.; Gokel,
W. G. J. Org. Chem. 1979, 44, 4640−4649. (c) Zupancic, B.; Kokalj,
M. Synthesis 1981, 1981, 913−915. (d) Guillot, R.; Loupy, A.;
Meddour, A.; Pellet, M.; Petit, A. Tetrahedron 2005, 61, 10129−
10137. (e) Ladhar, F.; Gharbi, E. Synth. Commun. 1991, 21, 413−417.
(f) D’Sa, B. A.; Kisanga, P.; Verkade, J. G. J. Org. Chem. 1998, 63,
3961−3967.
Muller, T. N. J. Am. Chem. Soc. 2002, 124, 8693−8698.
̈
(3) (a) Lanari, D.; Alonzi, M.; Ferlin, F.; Santoro, S.; Vaccaro, L.
Org. Lett. 2016, 18, 2680−2683. (b) Funabiki, T.; Hosomi, H.;
Yoshida, S.; Tarama, K. J. Am. Chem. Soc. 1982, 104, 1560−1568.
(c) Qin, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 15893−15895.
(d) Powell, K. J.; Han, Li-C; Sharma, P.; Moses, J. E. Org. Lett. 2014,
16, 2158−2161. (e) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S. I.
J. Am. Chem. Soc. 1989, 111, 5954−5955. (f) Sugahara, K.; Kimura,
T.; Kamata, K.; Yamaguchi, K.; Mizuno, N. Chem. Commun. 2012, 48,
8422−8424. (g) Tanaka, K.; Ono, N.; Kubo, A.; Kaji, A. Synthesis
1979, 1979, 890−891. (h) Ying, A.; Qiu, F.; Wu, C.; Hu, H.; Yang, J.
RSC Adv. 2014, 4, 33175−33183. (i) Villemin, D.; Jullien, A.; Bar, N.
Green Chem. 2003, 5, 467−469.
(c) Polshettiwar, V.; Varma, R. S. Green Chem. 2009, 11, 1313−
1316. (d) Ouali, A.; Majoral, J.; Caminade, A.; Taillefer, M.
ChemCatChem 2009, 1, 504−509. (e) Xu, Q.; Chen, J.; Liu, Q.
Adv. Synth. Catal. 2013, 355, 697−704. (f) Allen, L. J.; Crabtree, R. H.
Green Chem. 2010, 12, 1362−1364. (g) Bauer, H.; Alonso, M.; Färber,
C.; Elsen, H.; Pahl, J.; Causero, A.; Ballmann, G.; De Proft, F.;
Harder, S. Nat. Catal. 2018, 1, 40−47.
(14) A filtration experiment was performed to testify that the
reaction is not mediated by nanoparticles (see SI).
(4) Hartwig, J. Organotransition Metal Chemistry: From Bonding to
Catalysis; University Science Books: 2009.
(5) For selective reviews, see: (a) Guillena, G.; Ramon, D. J.; Yus,
M. Chem. Rev. 2010, 110, 1611−1641. (b) Gunanathan, C.; Milstein,
D. Science 2013, 341, 1229712. (c) Crabtree, R. H. Chem. Rev. 2017,
117, 9228−9246. (d) Alig, L.; Fritz, M.; Schneider, S. Chem. Rev.
2019, 119, 2681−2751. (e) Irrgang, T.; Kempe, R. Chem. Rev. 2019,
119, 2524−2549. (f) Ai, W.; Zhong, R.; Liu, X.; Liu, Q. Chem. Rev.
2019, 119, 2876−2953. (g) Junge, K.; Papa, V.; Beller, M. Chem. -
Eur. J. 2019, 25, 122−143.
(6) For selective cases, see: (a) Zhang, G.; Hanson, S. K. Org. Lett.
2013, 15, 650−653. (b) Mukherjee, A.; Nerush, A.; Leitus, G.;
Shimon, L. J. W.; Ben-David, Y.; Espinosa Jalapa, N. A.; Milstein, D. J.
Am. Chem. Soc. 2016, 138, 4298−4301. (c) Elangovan, S.; Neumann,
J.; Sortais, J.-B.; Junge, K.; Darcel, C.; Beller, M. Nat. Commun. 2016,
7, 12641. (d) Rösler, S.; Ertl, M.; Irrgang, T.; Kempe, R. Angew.
Chem., Int. Ed. 2015, 54, 15046−15050. (e) Yan, T.; Feringa, B. L.;
Barta, K. Nat. Commun. 2014, 5, 5602. (f) Samuelsen, S.; Santilli, C.;
Ahlquist, M. S. G.; Madsen, R. Chem. Sci. 2019, 10, 1150−1157.
(7) For selective cases, see: (a) Motokura, K.; Nishimura, D.; Mori,
K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. A. J. Am. Chem. Soc. 2004,
126, 5662−5663. (b) Löfberg, C.; Grigg, R.; Whittaker, M. A.; Keep,
A.; Derrick, A. J. Org. Chem. 2006, 71, 8023−8027. (c) Li, F.; Zou, X.;
Wang, N. Adv. Synth. Catal. 2015, 357, 1405−1415. (d) Anxionnat,
B.; Gomez Pardo, D.; Ricci, G.; Cossy, J. Org. Lett. 2011, 13, 4084−
4087. (e) Buil, M. L.; Esteruelas, M. A.; Herrero, J.; Izquierdo, S.;
Pastor, I. M.; Yus, M. ACS Catal. 2013, 3, 2072−2075.
(f) Thiyagarajan, S.; Gunanathan, C. ACS Catal. 2018, 8, 2473−2478.
(8) (a) Bullock, R. M. Catalysis without Precious Metals; Wiley-VCH:
Weinheim, 2010. (b) Chirik, P.; Morris, R. Acc. Chem. Res. 2015, 48,
2495−2495.
(9) Chakraborty, S.; Das, U. K.; Ben-David, Y.; Milstein, D. J. Am.
Chem. Soc. 2017, 139, 11710−11713.
(10) Yadav, V.; Landge, V. G.; Subaramanian, M.; Balaraman, E.
ACS Catal. 2020, 10, 947−954.
5032
Org. Lett. 2021, 23, 5028−5032