Page 7 of 12
Journal of the American Chemical Society
1
2
3
4
5
6
7
8
(6) Reviews on removable directing groups: (a) Rousseau, G.;
Org. Chem. 2014, 79, 1521. (j) Liu, B.; Jiang, H.‐Z.; Shi, B.‐F. Org.
Biomol. Chem. 2014, 12, 2538. (k) Zhang, C.; Sun, P. J. Org. Chem.
2014, 79, 8457. (l) Zhang, W.; Zhang, J.; Ren, S.; Liu, Y. J. Org.
Chem. 2014, 79, 11508. (m) Xu, Y.; Liu, P.; Li, S.‐L.; Sun, P. J. Org.
Chem. DOI: 10.1021/jo5026095.
(12) O‐ to N‐alkyl migratory rearrangement of alkyl pyridyl
ethers have been reported. See: (a) Yeung, C. S.; Hsieh, T. H. H.;
Dong, V. M. Chem. Sci. 2011, 2, 544. (b) Pan, S.; Ryu, N.; Shibata,
T. Org. Lett. 2013, 15, 1902.
(13) Electron defficient C‐O is normally more reactive. See: (a)
Sergeev, A. G.; Hartwig, J. F. Science 2011, 332, 439. (b) Sergeev, A.
G.; Webb, J. D.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 20226.
(14) The cleavage of highly electron‐defficient triazynyl ether
moiety was reproted to proceed under Ni catalysis: (a) Li, X.‐J.;
Zhang, J.‐L.; Geng, Y.; Jin, Z. J. Org. Chem. 2013, 78, 5078. (b)
Iranpoor, N.; Panahi, F. Adv. Synth. Catal. 2014, 356, 3067.
(15) (a) Tobisu, M.; Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2006,
128, 8152. (b) Tobisu, M.; Kita, Y.; Ano, Y.; Chatani, N. J. Am.
Chem. Soc. 2008, 130, 15982. (c) Tobisu, M.; Nakamura, R.; Kita,
Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 3174. (d) Kita, Y.; To‐
bisu, M.; Chatani, N. Org. Lett. 2010, 12, 1864. (e) Tobisu, M.;
Nakamura, R.; Kita, Y.; Chatani, N. Bull. Korean Chem. Soc. 2010,
31, 582. (f) Tobisu, M.; Hasegawa, J.; Kita, Y.; Kinuta, H.; Chatani,
N. Chem. Commun. 2012, 48, 11437.
(16) (a) Tobisu, M.; Kinuta, H.; Kita, Y.; Rémond, E.; Chatani, N. J.
Am. Chem. Soc. 2012, 134, 115. (b) Kinuta, H.; Kita, Y.; Rémond, E.;
Tobisu, M.; Chatani, N. Synthesis 2012, 44, 2999.
(17) (a) Taw, F. L.; White, P. S.; Bergman, R. G.; Brookhart, M. J.
Am. Chem. Soc. 2002, 124, 4192. (b) Taw, F. L.; Mueller, A. H.;
Bergman, R. G.; Brookhart, M. J. Am. Chem. Soc. 2003, 125, 9808.
(18) (a) Zhao, Y.; Cheng, X.; Li, L.; Li, Z. J. Mol. Struct.
THEOCHEM 2010, 941, 66. (b) Zhang, S.‐L.; Huang, L.; Bie, W.‐F.
Organometallics 2014, 33, 3030.
(19) (a) Jiang, Y.‐Y.; Yu, H.‐Z.; Fu, Y. Organometallics 2013, 32,
926. (b) Kinuta, H.; Takahashi, H.; Tobisu, M.; Mori, S.; Chatani,
N. Bull. Chem. Soc. Jpn. 2014, 87, 655.
(20) Related iron‐mediated C‐CN cleavage reactions: (a) Naka‐
zawa, H.; Kawasaki, T.; Miyoshi, K.; Suresh, C. H.; Koga, N. Or‐
ganometallics 2004, 23, 117. (b) Itazaki, M.; Nakazawa, H. Chem.
Lett. 2005, 34, 1054. (c) Nakazawa, H.; Kamata, K.; Itazaki, M.
Chem. Commun. 2005, 0, 4004. (d) Nakazawa, H.; Itazaki, M.;
Kamata, K.; Ueda, K. Chem. Asian J. 2007, 2, 882.
Breit, B. Angew. Chem., Int. Ed. 2011, 50, 2450. (b) Wang, C.;
Huang, Y. Synlett 2013, 24, 145. (c) Zhang, F.; Spring, D. R. Chem.
Soc. Rev. 2014, 43, 6906.
(7) (a) Itami, K.; Mitsudo, K.; Nokami, T.; Kamei, T.; Koike, T.;
Yoshida, J.‐i. J. Organomet. Chem. 2002, 653, 105. (b) Chernyak,
N.; Dudnik, A. S.; Huang, C.; Gevorgyan, V. J. Am. Chem. Soc.
2010, 132, 8270. (c) Dudnik, A. S.; Chernyak, N.; Huang, C.; Ge‐
vorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 8729. (d) Gulevich,
A. V.; Melkonyan, F. S.; Sarkar, D.; Gevorgyan, V. J. Am. Chem.
Soc. 2012, 134, 5528. (e) Sarkar, D.; Melkonyan, F. S.; Gulevich, A.
V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2013, 52, 10800.
(8) (a) Chatani, N.; Asaumi, T.; Ikeda, T.; Yorimitsu, S.; Ishii, Y.;
Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12882. (b)
Chatani, N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.;
Murai, S. J. Am. Chem. Soc. 2001, 123, 10935. (c) Chatani, N.; Yo‐
rimitsu, S.; Asaumi, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2002,
67, 7557. (d) Sagnes, C.; Fournet, G.; Joseph, B. Synlett 2009,
2009, 433. (e) Chen, J.; Song, G.; Pan, C.‐L.; Li, X. Org. Lett. 2010,
12, 5426. (f) Chen, J.; Pang, Q.; Sun, Y.; Li, X. J. Org. Chem. 2011,
76, 3523. (g) Chu, J.‐H.; Lin, P.‐S.; Lee, Y.‐M.; Shen, W.‐T.; Wu,
M.‐J. Chem.–Eur. J. 2011, 17, 13613. (h) Kawamorita, S.; Miyazaki,
T.; Iwai, T.; Ohmiya, H.; Sawamura, M. J. Am. Chem. Soc. 2012,
134, 12924. (i) Kim, S. H.; Park, S. H.; Chang, S. Tetrahedron 2012,
68, 5162. (j) Peschiulli, A.; Smout, V.; Storr, T. E.; Mitchell, E. A.;
Eliáš, Z.; Herrebout, W.; Berthelot, D.; Meerpoel, L.; Maes, B. U.
W. Chem.–Eur. J. 2013, 19, 10378. (k) Punji, B.; Song, W.;
Shevchenko, G. A.; Ackermann, L. Chem.–Eur. J. 2013, 19, 10605.
(l) Liang, D.; He, Y.; Zhu, Q. Org. Lett. 2014, 16, 2748. (m) Xu, H.;
Qiao, X.; Yang, S.; Shen, Z. J. Org. Chem. 2014, 79, 4414.
(9) It requires multistep for the removal of pyridyl group: (a)
Prokopcová, H.; Bergman, S. D.; Aelvoet, K.; Smout, V.; Herre‐
bout, W.; Van der Veken, B.; Meerpoel, L.; Maes, B. U. W.
Chem.–Eur. J. 2010, 16, 13063. (b) Chu, J.‐H.; Wu, C.‐C.; Chang,
D.‐H.; Lee, Y.‐M.; Wu, M.‐J. Organometallics 2012, 32, 272. (c)
Koley, M.; Dastbaravardeh, N.; Schnürch, M.; Mihovilovic, M. D.
ChemCatChem 2012, 4, 1345. (d) Chu, J.‐H.; Huang, H.‐P.; Hsu,
W.‐T.; Chen, S.‐T.; Wu, M.‐J. Organometallics 2014, 33, 1190. (e)
Odani, R.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed.
2014, 53, 10784. (f) Schinkel, M.; Wang, L.; Bielefeld, K.; Acker‐
mann, L. Org. Lett. 2014, 16, 1876.
(10) A 2‐Pyrimidyl group has also been developed as a removable
directing group, however, it requires the use of strong bases: (a)
Ackermann, L.; Lygin, A. V. Org. Lett. 2011, 13, 3332. (b) Acker‐
mann, L.; Lygin, A. V. Org. Lett. 2012, 14, 764. (c) Nishino, M.;
Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2012, 51,
6993. (d) Wang, Z.; Song, F.; Zhao, Y.; Huang, Y.; Yang, L.; Zhao,
D.; Lan, J.; You, J. Chem.–Eur. J. 2012, 18, 16616. (e) Xu, S.; Huang,
X.; Hong, X.; Xu, B. Org. Lett. 2012, 14, 4614. (f) Kou, X.; Zhao,
M.; Qiao, X.; Zhu, Y.; Tong, X.; Shen, Z. Chem.–Eur. J. 2013, 19,
16880. (g) Pan, C.; Jin, H.; Xu, P.; Liu, X.; Cheng, Y.; Zhu, C. J.
Org. Chem. 2013, 78, 9494. (h) Pospech, J.; Tlili, A.; Spannenberg,
A.; Neumann, H.; Beller, M. Chem.–Eur. J. 2014, 20, 3135. (i) Yu,
S.; Li, X. Org. Lett. 2014, 16, 1200.
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(21) Reviews on transition‐metal silyl complex: (a) Corey, J. Y.;
Braddock‐Wilking, J. Chem. Rev. 1998, 99, 175. (b) Osakada, K. J.
Organomet. Chem. 2000, 611, 323.
(22) Stoichiometric reactions using silylrhodium species: (a)
Kono, H.; Wakao, N.; Ojima, I.; Nagai, Y. Chem. Lett. 1975, 4, 189.
(b) Ruiz, J.; Bentz, P. O.; Mann, B. E.; Spencer, C. M.; Taylor, B.
F.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1987, 2709. (c)
Thorn, D. L.; Harlow, R. L. Inorg. Chem. 1990, 29, 2017.
(d)
Okazaki, M.; Ohshitanai, S.; Tobita, H.; Ogino, H. Chem. Lett.
2001, 30, 952. (e) Nishihara, Y.; Takemura, M.; Osakada, K. Or‐
ganometallics 2002, 21, 825. (f) Okazaki, M.; Ohshitanai, S.; To‐
bita, H.; Ogino, H. J. Chem. Soc., Dalton Trans. 2002, 2061. (g)
Raza, A. L.; Panetier, J. A.; Teltewskoi, M.; Macgregor, S. A.;
Braun, T. Organometallics 2013, 32, 3795.
(23) Reviews on transition‐metal boryl complex: (a) Braun‐
schweig, H. Angew. Chem., Int. Ed. 1998, 37, 1786. (b) Irvine, G. J.;
Lesley, M. J. G.; Marder, T. B.; Norman, N. C.; Rice, C. R.; Robins,
E. G.; Roper, W. R.; Whittell, G. R.; Wright, L. J. Chem. Rev. 1998,
98, 2685. (c) Braunschweig, H.; Colling, M. Coord. Chem. Rev.
2001, 223, 1. (d) Aldridge, S.; Coombs, D. L. Coord. Chem. Rev.
2004, 248, 535. (e) Braunschweig, H.; Kollann, C.; Rais, D. Angew.
Chem., Int. Ed. 2006, 45, 5254. (f) Braunschweig, H.; Dewhurst, R.
(11) (a) Kakiuchi, F.; Igi, K.; Matsumoto, M.; Hayamizu, T.;
Chatani, N.; Murai, S. Chem. Lett. 2002, 31, 396. (b) Gu, S.; Chen,
C.; Chen, W. J. Org. Chem. 2009, 74, 7203. (c) Chu, J.‐H.; Lin, P.‐
S.; Wu, M.‐J. Organometallics 2010, 29, 4058. (d) Ackermann, L.;
Diers, E.; Manvar, A. Org. Lett. 2012, 14, 1154. (e) Niu, L.; Yang,
H.; Wang, R.; Fu, H. Org. Lett. 2012, 14, 2618. (f) Kim, M.; Sharma,
S.; Park, J.; Kim, M.; Choi, Y.; Jeon, Y.; Kwak, J. H.; Kim, I. S. Tet‐
rahedron 2013, 69, 6552. (g) Ma, W.; Ackermann, L. Chem.–Eur. J.
2013, 19, 13925. (h) Yao, J.; Feng, R.; Wu, Z.; Liu, Z.; Zhang, Y. Adv.
Synth. Catal. 2013, 355, 1517. (i) Liu, B.; Jiang, H.‐Z.; Shi, B.‐F. J.
ACS Paragon Plus Environment