ACS Catalysis
Page 6 of 7
Sortais, J.ꢀB.; Junge, K.; Darcel, C.; Beller, M. Nat. Commun. 2016,
7, 12641; (c) Mukherjee, A.; Nerush, A.; Leitus, G.; Shimon, L. J. W.;
David, Y. B.; Jalapa, N. A. E.; Milstein, D. J. Am. Chem. Soc. 2016,
REFERENCES
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
3
3
4
4
4
4
4
4
4
4
4
4
5
5
5
5
5
5
5
5
5
5
6
(
1) Butters, M.; Catterick, D.; Craig, A.; Curzons, A.; Dale, D.;
Gillmore, A.; Green, S. P.; Marziano, I.; Sherlock, J. P.; White, W.
Chem. Rev. 2006, 106, 3002ꢀ3027.
(2) (a) Yang, Q.; Wanga, Q.; Yu, Z. Chem. Soc. Rev. 2015, 44,
1
38, 4298ꢀ4301; (d) Zhang, G.; Yin, Z.; Zheng, S. Org. Lett. 2016,18,
3
00ꢀ303; (e) Mastalir, M.; Tomsu, G.; Pittenauer, E.; Allmaier, G.;
Kirchner, K. Org. Lett. 2016,18, 3462ꢀ3465.
16) (a) Yu, D.ꢀG.; Wang, X.; Zhu, R.ꢀY.; Luo, S.; Zhang, X.ꢀB.;
Wang, B.ꢀQ.; Wang, L.; Shi, Z.ꢀJ. J. Am. Chem. Soc., 2012, 134,
4638ꢀ14641. For select examples of benzylic coupling, see: (b)
2
1
305ꢀ2329; (b) Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010,
10, 681ꢀ703; (c) Hamid, M. H. S. A.; Slatford, P. A.; Williams, J. M.
(
J. Adv. Synth. Catal. 2007, 349, 1555ꢀ1575; (d) Bähn, S.; Sebastian,
I.; Neubert, L.; Zhang, M.; Neumann, H.; Beller, M. ChemCatChem.
2011, 3, 1853ꢀ1864; (e) Guillena, G.; Ramon, D. J.; Yus, M. Chem.
Rev. 2010, 110, 1611ꢀ1641; (f) Gunanathan, C.; Milstein, D. Science
1
Guan, B.ꢀT.; Xiang, S.ꢀK.; Wang, B.ꢀQ.; Sun, Z.ꢀP.; Wang, Y.; Zhao,
K.ꢀQ.; Shi, Z.ꢀJ. J. Am. Chem. Soc., 2008, 130, 3268ꢀ3269; (c) Harris,
M. R.; Hanna, L. E.; Green, M. A.; Moore, C. E.; Jarvo, E. R. J. Am.
Chem. Soc., 2013, 135, 3303ꢀ3306; (d) Zhou, Q.; Srinivas, H. D.;
Dasgupta, S.; Watson, M. P. J. Am. Chem. Soc., 2013, 135, 3307ꢀ
2
2
013, 341, 249ꢀ260; (g) Watson, A. J. A.; Williams, J. M. J. Science
010, 329, 635ꢀ636.
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
(
(
3) Barta, K.; Ford, P. C. Acc. Chem. Res. 2014, 47, 1503ꢀ1512.
4) (a) Trost, B. M. Science 1991, 254, 1471ꢀ1477; (b) Anastas, P.
3
1
2
310; (e) León, T.; Correa, A.; Martin, R. J. Am. Chem. Soc., 2013,
35, 1221ꢀ1224; (f) Cao, Z.ꢀC.; Luo, Q.ꢀY.; Shi. Z.ꢀJ. Org. Lett.,
016, 18, 5978ꢀ5981 and references cited therein.
T.; Warner, J. C. Green Chemistry: Theory and Practice, Oxford
University Press, 1998; (c) Beller, M.; Centi, G. ChemSusChem 2009,
(
17) For selected reviews, see: (a) Tasker, S. Z.; Standley, E. A.;
2
, 459ꢀ460.
5) (a) J. L. McGuire, Pharmaceuticals: Classes, Therapeutic
Agents, Areas of Application, WileyꢀVCH, Weinheim, Germany,
000, Vols. 1ꢀ4. (b) Hansch, C.; Sammes, P. G.; Taylor, J. B. Com-
Jamison, T. F. Nature, 2014, 509, 299ꢀ309; (b) Valentine, A.; Ananiꢀ
kov, P. ACS Catal. 2015, 5, 1964ꢀ1971; (c) Jolly, P. W.; Wilke, G.
The Organic Chemistry of Nickel, Academic Press: New York, 1974;
(
2
(
d) Wilke, G. Angew. Chem., Int. Ed. 1988, 27, 185ꢀ206; (e) Tamaru,
prehensive Medicinal Chemistry, Pergamon Press, Oxford, 1990, Vol.
2, Chapter 7.1; (c) Ricci, A. Amino Group Chemistry: From Synthesis
to the Life Sciences; Eds.: WileyꢀVCH, Weinheim, 2008.
Y. Modern Organonickel Chemistry; Eds.: WileyꢀVCH, Weinheim,
Germany, 2005, pp 327; (f) Dander, J. E.; Garg, N. K. ACS Catal.,
2
017, 7, 1413ꢀ1423.
(
6) (a) Surry, D. S.; Buchwald, S. L. Angew. Chem. Int. Ed. 2008,
7, 6338ꢀ6361; (b) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852ꢀ860;
c) Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177ꢀ2250; (d)
(18) For reviews of Niꢀcatalyzed CꢀO bond activation, see: (a) Zarꢀ
4
(
ate, C.; Van Gemmeren, M.; Somerville, R. J.; Martin, R. Adv. Or-
ganomet. Chem. 2016, 66, 143ꢀ222; (b) Tobisu, M.; Chatani, N. Acc.
Chem. Res. 2015, 48, 1717ꢀ1726; (c) Tollefson, E. J.; Hanna, L. E.;
Jarvo, E. R. Acc. Chem. Res. 2015, 48, 2344ꢀ2353; (d) Su, B.; Cao,
Z.ꢀC.; Shi, Z.ꢀJ. Acc. Chem. Res. 2015, 48, 886ꢀ896; (e) Cornella, J.;
Zarate, C.; Martin, R. Chem. Soc. Rev. 2014, 43, 8081ꢀ8097; (f)
Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita,
A.ꢀM.; Garg, N. K.; Percec, V. Chem. Rev. 2011, 111, 1346ꢀ1416.
Sperotto, E.; van Klink, G. P. M.; van Koten, G.; de Vries, J. G. Dal-
ton Trans. 2010, 39, 10338ꢀ10351; (e) Huang, L.; Arndt, M.; Gooßen,
K.; Heydt, H.; Gooßen, L. J. Chem. Rev. 2015, 115, 2596ꢀ2697.
(
7) (a) Brown, D. G.; Boström, J. J. Med. Chem. 2016, 59,
443−4458; (b) Lawrence, S. A. Amines: Synthesis, Properties, and
Applications, Eds.: Cambridge University, Cambridge, 2006.
8) Bullock, R. M. Catalysis Without Precious Metals, Eds.:
4
(
(
19) For selected examples of Niꢀcatalyzed CꢀN bond formation
reactions, see: (a) Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc.
997, 119, 6054ꢀ6058; (b) Park, N. H.; Teverovskiy, G.; Buchwald, S.
WileyꢀVCH, Weinheim, 2010.
(9) Selected recent examples with Ruꢀcatalysts: (a) Jumde, V. R.;
Gonsalvi, L.; Guerriero, A.; Peruzzini, M.; Taddei, M. Eur. J. Org.
Chem. 2015, 2015, 1829ꢀ1833; (b) Jumde, V. R.; Cini, E.; Porcheddu,
A.; Taddei, M. Eur. J. Org. Chem. 2015, 2015, 1068ꢀ1074; (c) Balaꢀ
raman, E.; DiskinꢀPosner, D. S. Y.; Milstein, D. Catal. Lett. 2015,
145, 139ꢀ144; (d) Oldenhuis, N. J.; Dong, V. M.; Guan, Z. J. Am.
Chem. Soc. 2014, 136, 12548ꢀ12551; (e) Enyong, A. B.; Moasser, B.
J. Org. Chem. 2014, 79, 7553ꢀ7563.
1
L. Org. Lett. 2014, 16, 220ꢀ223; (c) Shimasaki, T.; Tobisu, M.;
Chatani, N. Angew. Chem., Int. Ed. 2010, 49, 2929ꢀ2932; (d) Barker,
T. J.; Jarvo, E. R. J. Am. Chem. Soc. 2009, 131, 15598ꢀ15599; (e)
Ramgren, S. D.; Silberstein, A. L.; Yang, Y.; Garg, N. K. Angew.
Chem., Int. Ed. 2011, 50, 2171ꢀ2173; (f) Mesganaw, T.; Silberstein,
A. L.; Ramgren, S. D.; Nathel, N. F.; Hong, X.; Liu, P.; Garg, N. K.
Chem. Sci. 2011, 2, 1766ꢀ1771.
(20) (a) Shimizu, K.; Kon, K.; Onodera, W.; Yamazaki, H.; Kondo,
J. N. ACS Catal. 2013, 3, 112ꢀ117; (b) Shimizu, K.; Imaiida, N.; Kon,
K.; Siddiki, S. M. A. H.; Satsuma, A. ACS Catal. 2013, 3, 998ꢀ1005.
(
10) Selected recent examples with Irꢀcatalysts: (a) Wöckel, S.;
Plessow, P.; Chelwies, M.; Brinks, M. K.; Rominger, F.; Hofmann,
P.; Limbach, M. ACS Catal. 2014, 4, 152ꢀ161; (b) Zhang, Y.; Lim,
C.ꢀS.; Sim, D. S. B.; Pan, H.ꢀJ.; Zhao, Y. Angew. Chem., Int. Ed.
2014, 53, 1399ꢀ1403; (c) Ruch, S.; Irrgang, T.; Kempe, R. Chem. -
Eur. J. 2014, 20, 13279ꢀ13285; (d) Chang, Y.ꢀH.; Nakajima, Y.;
Ozawa, F. Organometallics 2013, 32, 2210ꢀ2215.
(
21) Chakraborty, S.; Piszel, P. E.; Brennessel, W. W.; Jones, W.
D. Organometallics 2015, 34, 5203ꢀ5206.
22) (a) Vaughanjr, J. R. G.; Anderson, W.; Clapp, R. C.; Clark, J.
(
H.; English, J. P.; Howard, K. L.; Marson, H. W.; Sutherland, L. H.;
Denton, J. J. J. Org. Chem. 1949, 14, 228–234; (b) Parsons, M. E.;
Ganellin, C. R. Br. J. Pharmacol. 2006, 147, S127ꢀS135.
(
11) (a) Watanabe, Y.; Tsuji, Y.; Ohsugi, Y. Tetrahedron Lett.
1
981, 22, 2667ꢀ2670; (b) Grigg, R.; Mitchell, T. R. B.; Sutthivaiyakit,
S.; Tongpenyai, N. J. Chem. Soc. Chem. Commun. 1981, 611–612.
(12) For selected examples, see: (a) Fujita, K.ꢀI.; Fujii, T.; Yamaꢀ
guchi, R. Org. Lett. 2004, 6, 3525ꢀ3528; (b) Gnanamgari, D.; Sauer,
E. L. O.; Schley, N. D.; Butler, C.; Incarvito, C. D.; Crabtree, R. H.
Organometallics 2009, 28, 321ꢀ325; (c) Hamid, M. H. S. A.; Wilꢀ
liams, J. M. J. Chem. Commun. 2007, 725ꢀ727; (d) Gunanathan, C.;
Milstein, D. Angew. Chem., Int. Ed. 2008, 47, 8661ꢀ8664; (e) Kawaꢀ
hara, R.; Fujita, K.ꢀI.; Yamaguchi, R. J. Am. Chem. Soc. 2010, 132,
(
23) (a) Gunanathan, C.; Milstein, D. Science 2013, 341, 1229712;
b) Fujita, K.; Yamamoto, K.; Yamaguchi, R. Org. Lett. 2002, 4,
691ꢀ2694.
(
2
(24) Khrizanforov, M.; Khrizanforova, V.; Mamedov, V.; Zhukova,
N.; Strekalova, S.; Grinenko, V.; Gryaznova, T.; Sinyashin, O.; Budꢀ
nikova, Y. J. Organomet. Chem. 2016, 820, 82ꢀ88.
(
1
25) (a) Green, M. L. H.; Saito, T.; Tanfield, P. J. J. Chem. Soc. A
971, 152ꢀ154. (b) Lindner, M. M.; Beckmann, U.; Frank, W.; Kläui,
1
2
5
5108ꢀ15111.
13) Zhao, Y. S.; Foo, S. W.; Saito, S. Angew. Chem., Int. Ed.
011, 50, 3006ꢀ3009.
14) (a) Yan, T.; Feringa, B. L.; Barta, K. Nat. Commun. 2014, 5,
602.
(b) Rawlings, A. J.; Diorazio, L. J.; Wills, M. Org. Lett. 2015, 17,
W. ISRN Inorg. Chem. 2013, 1ꢀ13 (Article ID 732629;
http://dx.doi.org/10.1155/2013/732629)
(26) (a) Hamid, M. H. S. A.; Allen, C. L.; Lamb, G.W.; Maxwell,
A. C.; Maytum, H. C.; Watsom, A. J. A.; Williams, J. M. J. J. Am.
Chem. Soc. 2009, 131, 1766ꢀ1774; (b) Samec, J. S. M.; Backvall, J.ꢀ
E.; Andersson, P. G.; Brandt, P. Chem. Soc. Rev. 2006, 35, 237ꢀ248.
(
(
1
3
086ꢀ1089; (c) Yan, T.; Feringa, B. L.; Barta, K. ACS Catal. 2016, 6,
81ꢀ388.
(
27) (a) Simmons, E. M.; Hartwig, J. F. Angew. Chem., Int. Ed.
2012, 51, 3066ꢀ3072; (b) Wong, C. M.; McBurney, R. T.; Binding, S.
C.; Peterson, M. B.; Gonçales, V. R.; Gooding, J. J.; Messerle, B. A.
Green Chem. 2017, 19, 3142ꢀ3151; (c) Bartoszewicz, A.; Miera, G.
(
15) (a) Rosler, S.; Ertl, M.; Irrgang, T.; Kempe, R. Angew. Chem.
Int. Ed., 2015, 54, 15046ꢀ15050; (b) Elangovan. S.; Neumann. J.;
ACS Paragon Plus Environment