-
1
-
-
0004127624
-
-
For general reviews, see a, Plenum Press: New York
-
For general reviews, see (a) Colquhoun, H. M.; Thomson, D. J.; Twigg, M. V. Carbonylation: Direct Synthesis of Carbonyl Compounds; Plenum Press: New York, 1991.
-
(1991)
Carbonylation: Direct Synthesis of Carbonyl Compounds
-
-
Colquhoun, H.M.1
Thomson, D.J.2
Twigg, M.V.3
-
3
-
-
84942772095
-
-
Wilkinson, G, Stone, F. G. A, Abel, E. W, Eds, Pergamon Press: Oxford, U.K
-
(c) Tkatchenko, I. Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Vol. 8. pp 101-223.
-
(1982)
Comprehensive Organometallic Chemistry
, vol.8
, pp. 101-223
-
-
Tkatchenko, I.1
-
4
-
-
33846918696
-
-
Some recent reviews on C-H functionalizations, see a
-
Some recent reviews on C-H functionalizations, see (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
-
(2007)
Chem. Rev
, vol.107
, pp. 174
-
-
Alberico, D.1
Scott, M.E.2
Lautens, M.3
-
6
-
-
33750509858
-
-
(c) Yu, J.-Q.; Giri, R.; Chen, X. Org. Biomol. Chem. 2006, 4, 4041.
-
(2006)
Org. Biomol. Chem
, vol.4
, pp. 4041
-
-
Yu, J.-Q.1
Giri, R.2
Chen, X.3
-
8
-
-
0036589261
-
-
(d) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
-
(2002)
Chem. Rev
, vol.102
, pp. 1731
-
-
Ritleng, V.1
Sirlin, C.2
Pfeffer, M.3
-
11
-
-
7744224233
-
-
Orito, K.; Horibata, A.; Nakamura, T.; Ushito, H.; Nagasaki, H.; Yuguchi, M.; Yamashita, S.; Tokuda, M. J. Am. Chem. Soc. 2004, 126, 14342.
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 14342
-
-
Orito, K.1
Horibata, A.2
Nakamura, T.3
Ushito, H.4
Nagasaki, H.5
Yuguchi, M.6
Yamashita, S.7
Tokuda, M.8
-
12
-
-
3042704672
-
-
Selected examples for transition metal catalyzed direct carbonylation reactions: for [Ru] (a) Asaumi, T.; Matsuo, T.; Fukuyama, T.; Ie, Y.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 4433 and references therein.
-
Selected examples for transition metal catalyzed direct carbonylation reactions: for [Ru] (a) Asaumi, T.; Matsuo, T.; Fukuyama, T.; Ie, Y.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 4433 and references therein.
-
-
-
-
13
-
-
41449097173
-
-
For [Pd
-
(b) For [Pd]
-
-
-
-
14
-
-
0034867872
-
-
(c) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
-
(2001)
Acc. Chem. Res
, vol.34
, pp. 633
-
-
Jia, C.1
Kitamura, T.2
Fujiwara, Y.3
-
15
-
-
0001366689
-
-
(d) Fujiwara, Y.; Takaki, K.; Taniguchi, Y. Synlett 1996, 7, 591.
-
(1996)
Synlett
, vol.7
, pp. 591
-
-
Fujiwara, Y.1
Takaki, K.2
Taniguchi, Y.3
-
16
-
-
0000386089
-
-
For [Rh] (e) Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1996, 61, 6941.
-
For [Rh] (e) Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1996, 61, 6941.
-
-
-
-
17
-
-
0343535251
-
Mo], and [Cr] (f) Mori, Y.; Tsuji, J
-
For [Co
-
For [Co], [Mo], and [Cr] (f) Mori, Y.; Tsuji, J. Tetrahedron 1971, 27, 3811.
-
(1971)
Tetrahedron
, vol.27
, pp. 3811
-
-
-
18
-
-
34249056813
-
-
For recent examples a
-
For recent examples (a) Yang, S.; Li, B.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 6066.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 6066
-
-
Yang, S.1
Li, B.2
Wan, X.3
Shi, Z.4
-
19
-
-
34547883488
-
-
(b) Chiong, H. A.; Pham, Q.-N.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 9879.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 9879
-
-
Chiong, H.A.1
Pham, Q.-N.2
Daugulis, O.3
-
20
-
-
33947644069
-
-
(c) Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007, 129, 3510.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 3510
-
-
Giri, R.1
Maugel, N.2
Li, J.-J.3
Wang, D.-H.4
Breazzano, S.P.5
Saunders, L.B.6
Yu, J.-Q.7
-
21
-
-
30744445455
-
-
(d) Chen, X.; Li, J.-J.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 78.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 78
-
-
Chen, X.1
Li, J.-J.2
Hao, X.-S.3
Goodhue, C.E.4
Yu, J.-Q.5
-
22
-
-
33749509027
-
-
(e) Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 12634
-
-
Chen, X.1
Goodhue, C.E.2
Yu, J.-Q.3
-
24
-
-
25444458063
-
-
(g) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 13154
-
-
Zaitsev, V.G.1
Shabashov, D.2
Daugulis, O.3
-
25
-
-
19744365933
-
-
(h) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 7330
-
-
Kalyani, D.1
Deprez, N.R.2
Desai, L.V.3
Sanford, M.S.4
-
26
-
-
21244438753
-
-
(i) Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
-
(2005)
Angew. Chem., Int. Ed
, vol.44
, pp. 4046
-
-
Daugulis, O.1
Zaitsev, V.G.2
-
27
-
-
33746071928
-
-
For selected examples, see a
-
For selected examples, see (a) Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 9048
-
-
Thu, H.-Y.1
Yu, W.-Y.2
Che, C.-M.3
-
28
-
-
33947689674
-
-
(b) Dick, A. R.; Remy, M. S.; Kampf, J. W.; Sanford, M. S. Organometallics 2007, 26, 1365.
-
(2007)
Organometallics
, vol.26
, pp. 1365
-
-
Dick, A.R.1
Remy, M.S.2
Kampf, J.W.3
Sanford, M.S.4
-
29
-
-
33745577893
-
-
(c) Kalyani, D.; Dick, A. R.; Anani, W. Q.; Sanford, M. S. Org. Lett. 2006, 8, 2523.
-
(2006)
Org. Lett
, vol.8
, pp. 2523
-
-
Kalyani, D.1
Dick, A.R.2
Anani, W.Q.3
Sanford, M.S.4
-
30
-
-
33744928374
-
-
(d) Hull, K. L.; Anani, W. Q.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 7134.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 7134
-
-
Hull, K.L.1
Anani, W.Q.2
Sanford, M.S.3
-
31
-
-
33746872900
-
-
(e) Reddy, B. V. S.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391.
-
(2006)
Org. Lett
, vol.8
, pp. 3391
-
-
Reddy, B.V.S.1
Reddy, L.R.2
Corey, E.J.3
-
32
-
-
17044366225
-
-
(f) Giri, R.; Chen, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 2112.
-
(2005)
Angew. Chem., Int. Ed
, vol.44
, pp. 2112
-
-
Giri, R.1
Chen, X.2
Yu, J.-Q.3
-
33
-
-
3543057683
-
-
(g) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542.
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 9542
-
-
Desai, L.V.1
Hull, K.L.2
Sanford, M.S.3
-
34
-
-
1542345322
-
-
(h) Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300.
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 2300
-
-
Dick, A.R.1
Hull, K.L.2
Sanford, M.S.3
-
35
-
-
21944441002
-
-
For reviews, see a
-
For reviews, see (a) Dupont, J.; Consorti, C. S.; Spenser, J. Chem. Rev. 2005, 105, 2527.
-
(2005)
Chem. Rev
, vol.105
, pp. 2527
-
-
Dupont, J.1
Consorti, C.S.2
Spenser, J.3
-
37
-
-
41449103531
-
-
12] (5 mol%) and DEAD in toluene did not produce 2a in detectable yield with the starting material being recovered (87%).
-
12] (5 mol%) and DEAD in toluene did not produce 2a in detectable yield with the starting material being recovered (87%).
-
-
-
-
38
-
-
0042771960
-
-
Ricci, A, Ed, Wiley-VCH: Weinheim, Germany, Chapter 3, p
-
Genet, J.-P.; Greek, C.; Lavergne, D. In Modern Amination Method; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000; Chapter 3, p 65.
-
(2000)
Modern Amination Method
, pp. 65
-
-
Genet, J.-P.1
Greek, C.2
Lavergne, D.3
-
39
-
-
34548217139
-
-
2 to dibenzyl azodicarboxylate: Muniz, K.; Iglesias, A. Angew. Chem., Int. Ed. 2007, 46, 6350.
-
2 to dibenzyl azodicarboxylate: Muniz, K.; Iglesias, A. Angew. Chem., Int. Ed. 2007, 46, 6350.
-
-
-
-
40
-
-
41449086051
-
-
See Supporting Information for details
-
See Supporting Information for details.
-
-
-
-
41
-
-
41449084393
-
-
2-Et (X-ray structure characterized) was isolated asa side-product in 52% yield from the Pd-catalyzed reaction of 1a with DEAD.
-
2-Et (X-ray structure characterized) was isolated asa side-product in 52% yield from the Pd-catalyzed reaction of 1a with DEAD.
-
-
-
-
42
-
-
25444475266
-
-
Similar regioselectivity was also reported by Sanford and co-workers for Pd-catalyzed acetoxylation of arylpyridines: Kalyani, D.; Sanford, M. Org. Lett. 2005, 7, 4149. See also refs 5, 6a, and 6c
-
Similar regioselectivity was also reported by Sanford and co-workers for Pd-catalyzed acetoxylation of arylpyridines: Kalyani, D.; Sanford, M. Org. Lett. 2005, 7, 4149. See also refs 5, 6a, and 6c
-
-
-
-
43
-
-
41449094630
-
-
This result may suggest that the higher reactivity of DEAD relative to other azodicarboxylates could have led to the higher product yields observed see Supporting Information
-
This result may suggest that the higher reactivity of DEAD relative to other azodicarboxylates could have led to the higher product yields observed (see Supporting Information).
-
-
-
-
44
-
-
41449117409
-
-
13C NMR analysis of the unknown revealed a characteristic carbonyl signal at 155.8 ppm, which is unique from dibenzyl carbonate and dibenzyl oxalate. A similar product profile was observed for thermal decomposition of dibenzyl azodicarboxylate.
-
13C NMR analysis of the unknown revealed a characteristic carbonyl signal at 155.8 ppm, which is unique from dibenzyl carbonate and dibenzyl oxalate. A similar product profile was observed for thermal decomposition of dibenzyl azodicarboxylate.
-
-
-
-
48
-
-
0001806998
-
-
For alternative routes to alkoxyacyl radical formation: a
-
For alternative routes to alkoxyacyl radical formation: (a) Morihovitis, T.; Schiesser, C. H.; Skidmore, M. A. J. Chem. Soc., Perkin Trans. 2 1999, 2041.
-
(1999)
J. Chem. Soc., Perkin Trans. 2
, pp. 2041
-
-
Morihovitis, T.1
Schiesser, C.H.2
Skidmore, M.A.3
-
51
-
-
84992264173
-
-
Recent reports on metal catalyzed alkane carbonylation by a free-radical mechanism: (a) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350.
-
Recent reports on metal catalyzed alkane carbonylation by a free-radical mechanism: (a) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350.
-
-
-
-
53
-
-
0002521519
-
-
IV chemistry, see (a) Canty, A. J. Acc. Chem. Res. 1992, 25, 83.
-
IV chemistry, see (a) Canty, A. J. Acc. Chem. Res. 1992, 25, 83.
-
-
-
-
54
-
-
34248577469
-
-
For recent examples, see: b
-
For recent examples, see: (b) Welbes, L. L.; Lyons, T. W.; Cychosz, K. A.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 5836.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 5836
-
-
Welbes, L.L.1
Lyons, T.W.2
Cychosz, K.A.3
Sanford, M.S.4
-
55
-
-
34247542965
-
-
(c) Tong, X.; Beller, M.; Tse, M. K. J. Am. Chem. Soc. 2007, 129, 4906.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 4906
-
-
Tong, X.1
Beller, M.2
Tse, M.K.3
|