-
1
-
-
20544450502
-
-
2nd ed, de Meijere, A, Diederich, F, Eds, Wiley-VCH: Weinheim
-
Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions
-
-
-
2
-
-
0034867872
-
-
For recent reviews, see: a
-
For recent reviews, see: (a) 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
-
3
-
-
0036589261
-
-
(b) 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
-
5
-
-
33750509858
-
-
(d) 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
-
6
-
-
33846918696
-
-
(e) 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
-
7
-
-
34447131678
-
-
(f) Herrerias, C. I.; Yao, X.; Li, Z.; Li, C.-J. Chem. Rev. 2007, 107, 2546.
-
(2007)
Chem. Rev
, vol.107
, pp. 2546
-
-
Herrerias, C.I.1
Yao, X.2
Li, Z.3
Li, C.-J.4
-
9
-
-
4644355479
-
-
For examples of oxidative C-C bond-formation reactions using peroxides as the terminal oxidant, see: (a) Li, Z, Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810
-
For examples of oxidative C-C bond-formation reactions using peroxides as the terminal oxidant, see: (a) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810.
-
-
-
-
14
-
-
27544488753
-
-
(f) Murahashi, S.-I.; Komiya, N.; Terai, H. Angew. Chem. Int. Ed. 2005, 44, 6931.
-
(2005)
Angew. Chem. Int. Ed
, vol.44
, pp. 6931
-
-
Murahashi, S.-I.1
Komiya, N.2
Terai, H.3
-
16
-
-
33745157509
-
-
(h) Li, Z.; Bohle, D. S.; Li, C.-J. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 8928.
-
(2006)
Proc. Natl. Acad. Sci. U.S.A
, vol.103
, pp. 8928
-
-
Li, Z.1
Bohle, D.S.2
Li, C.-J.3
-
18
-
-
34548356423
-
-
(j) Li, Z.; Cao, L.; Li, C.-J. Angew. Chem. Int. Ed. 2007, 46, 6505.
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 6505
-
-
Li, Z.1
Cao, L.2
Li, C.-J.3
-
19
-
-
53549084027
-
-
(k) Deng, G.; Zhao, L.; Li, C.-J. Angew. Chem. Int. Ed. 2008, 47, 6278.
-
(2008)
Angew. Chem. Int. Ed
, vol.47
, pp. 6278
-
-
Deng, G.1
Zhao, L.2
Li, C.-J.3
-
21
-
-
54749149062
-
-
(m) Li, Z.; Yu, R.; Li, H. Angew. Chem. Int. Ed. 2008, 47, 7497.
-
(2008)
Angew. Chem. Int. Ed
, vol.47
, pp. 7497
-
-
Li, Z.1
Yu, R.2
Li, H.3
-
23
-
-
33645461780
-
-
For examples of oxidative C-C bond-formation reactions using DDQ as the terminal oxidant, see: (a) Zhang, Y, Li, C.-J. J. Am. Chem. Soc. 2006, 128, 4242
-
For examples of oxidative C-C bond-formation reactions using DDQ as the terminal oxidant, see: (a) Zhang, Y.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 4242.
-
-
-
-
27
-
-
0346850026
-
-
(a) Murahashi, S.-I.; Komiya, N.; Terai, H.; Nakae, T. J. Am. Chem. Soc. 2003, 125, 15312.
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 15312
-
-
Murahashi, S.-I.1
Komiya, N.2
Terai, H.3
Nakae, T.4
-
29
-
-
50249118196
-
-
(c) Murahashi, S.-I.; Nakae, T.; Terai, H.; Komiya, N. J. Am. Chem. Soc. 2008, 130, 11005.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 11005
-
-
Murahashi, S.-I.1
Nakae, T.2
Terai, H.3
Komiya, N.4
-
31
-
-
0000434277
-
-
For reviews on the use of NHPI as an effective catalyst for oxidation of C-H bonds in oxygen, see: a
-
For reviews on the use of NHPI as an effective catalyst for oxidation of C-H bonds in oxygen, see: (a) Ishii, Y.; Sakaguchi, S.; Iwahama, T. Adv. Synth. Catal. 2001, 343, 393.
-
(2001)
Adv. Synth. Catal
, vol.343
, pp. 393
-
-
Ishii, Y.1
Sakaguchi, S.2
Iwahama, T.3
-
32
-
-
53549097389
-
-
(b) Galli, C.; Gentili, P.; Lanzalunga, O. Angew. Chem. Int. Ed. 2008, 47, 4790.
-
(2008)
Angew. Chem. Int. Ed
, vol.47
, pp. 4790
-
-
Galli, C.1
Gentili, P.2
Lanzalunga, O.3
-
33
-
-
33751154737
-
-
For representative examples of NHPI as an effective catalyst for oxidation of C-H bonds in oxygen, see: a
-
For representative examples of NHPI as an effective catalyst for oxidation of C-H bonds in oxygen, see: (a) Ishii, Y.; Nakayama, K.; Takeno, M.; Sakaguchi, S.; Iwahama, T.; Nishiyama, Y. J. Org. Chem. 1995, 60, 3934.
-
(1995)
J. Org. Chem
, vol.60
, pp. 3934
-
-
Ishii, Y.1
Nakayama, K.2
Takeno, M.3
Sakaguchi, S.4
Iwahama, T.5
Nishiyama, Y.6
-
34
-
-
0000828619
-
-
(b) Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama, K.; Nishiyama, Y. J. Org. Chem. 1996, 61, 4520.
-
(1996)
J. Org. Chem
, vol.61
, pp. 4520
-
-
Ishii, Y.1
Iwahama, T.2
Sakaguchi, S.3
Nakayama, K.4
Nishiyama, Y.5
-
35
-
-
0000074729
-
-
(c) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222.
-
(1998)
J. Org. Chem
, vol.63
, pp. 222
-
-
Kato, S.1
Iwahama, T.2
Sakaguchi, S.3
Ishii, Y.4
-
36
-
-
0035825184
-
-
(d) Sakaguchi, S.; Nishiwaki, Y.; Kitamura, T.; Ishii, Y. Angew. Chem. Int. Ed. 2001, 40, 222.
-
(2001)
Angew. Chem. Int. Ed
, vol.40
, pp. 222
-
-
Sakaguchi, S.1
Nishiwaki, Y.2
Kitamura, T.3
Ishii, Y.4
-
37
-
-
0035929451
-
-
(e) Hara, T.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2001, 66, 6425.
-
(2001)
J. Org. Chem
, vol.66
, pp. 6425
-
-
Hara, T.1
Iwahama, T.2
Sakaguchi, S.3
Ishii, Y.4
-
38
-
-
4544230894
-
-
(f) Hirabayashi, T.; Sakaguchi, S.; Ishii, Y. Angew. Chem. Int. Ed. 2004, 43, 1120.
-
(2004)
Angew. Chem. Int. Ed
, vol.43
, pp. 1120
-
-
Hirabayashi, T.1
Sakaguchi, S.2
Ishii, Y.3
-
39
-
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3.
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3.
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62349134909
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Representative Procedure and Spectroscopic Data, Synthesis of Dimethyl 2-(3,4-Dihydro-1H-isochromen-1-yl)malonate (3a) In a sealable test tube equipped with a magnetic stir bar was charged Cu(OTf) 2 (9.5 mg, 0.026 mmol, InCl3 (5.8 mg, 0.026 mmol, and NHPI (17.1 mg, 0.105 mmol, The reaction vessel was sealed and flushed with O2. The tube was attached to a balloon of O2 and charged with dimethyl malonate (1a, 0.060 mL, 0.524 mmol) and isochroman (2a, 0.33 mL, 2.6 mmol, The test tube was placed in an oil bath set at 55°C and was allowed to stir overnight. The reaction mixture was allowed to cooled to r.t. and the crude reaction mixture was purified by silica gel column chromatography (EtOAc-hexane, 1:4) to provide the desired alkylation product 3a (107.1 mg, 0.405 mmol, 77, as a clear colorless oil. 1H NMR (400 MHz, CDCl3, δ, 7.18-7.08 (m, 3 H, 6.99 d, J
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5b
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62349116906
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Representative Procedure and Spectroscopic Data, Synthesis of 2-(2,4-dihydro-1H-isochromen-1-yl)-1-phenylethanone (5a) In a sealable test tube equipped with a magnetic stir bar was charged Cu(OTf) 2 (9.0 mg, 0.025 mmol, InCl3 (5.5 mg, 0.025 mmol, and NHPI (16.3 mg, 0.100 mmol, The reaction vessel was sealed and flushed with O2. The tube was attached to a balloon of O2 and charged with acetophenone (4a, 0.058 mL, 0.500 mmol) and isochroman (2a, 0.31 mL, 2.5 mmol, The test tube was placed in an oil bath set at 75°C and was allowed to stir overnight. The reaction mixture was allowed to cooled to r.t, and the crude reaction mixture was purified by silica gel column chromatography (EtOAc-hexane, 1:5) to provide the desired alkylation product 5a (95.0 mg, 0.379 mmol, 75, as a pale yellow oil. 1H NMR (400 MHz, CDCl 3, δ, 8.03-8.00 (m, 2 H, 7.59-7.55 (m, 1 H, 7.49-7.45 m
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5a
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Previously, we proposed a similar intermediate for the oxidative arylation of cyclic benzyl amines with aryl boronic acids.6d
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6d
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Although alcohol 6 was not observed during the optimization process, we considered it to be a potential intermediate since benzylic alcohols are known to undergo alkylation with malonates and diketones in the presence of metal salts. For recent examples, see: (a) Yasuda, M, Somyo, T, Baba, A. Angew. Chem. Int. Ed. 2006, 45, 793
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Although alcohol 6 was not observed during the optimization process, we considered it to be a potential intermediate since benzylic alcohols are known to undergo alkylation with malonates and diketones in the presence of metal salts. For recent examples, see: (a) Yasuda, M.; Somyo, T.; Baba, A. Angew. Chem. Int. Ed. 2006, 45, 793.
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(b) Rueping, M.; Nachtsheim, B. J.; Kuenkel, A. Org. Lett. 2007, 9, 825.
-
(2007)
Org. Lett
, vol.9
, pp. 825
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Rueping, M.1
Nachtsheim, B.J.2
Kuenkel, A.3
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(c) Kischel, J.; Mertins, K.; Michalik, D.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2007, 349, 865.
-
(2007)
Adv. Synth. Catal
, vol.349
, pp. 865
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Kischel, J.1
Mertins, K.2
Michalik, D.3
Zapf, A.4
Beller, M.5
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(d) Huang, W.; Wang, J.; Shen, Q.; Zhou, X. Tetrahedron Lett. 2007, 48, 3969.
-
(2007)
Tetrahedron Lett
, vol.48
, pp. 3969
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Huang, W.1
Wang, J.2
Shen, Q.3
Zhou, X.4
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47
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(e) Noji, M.; Konno, Y.; Ishii, K. J. Org. Chem. 2007, 72, 5161.
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(2007)
J. Org. Chem
, vol.72
, pp. 5161
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Noji, M.1
Konno, Y.2
Ishii, K.3
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48
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0027246051
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For the preparation of benzylic alcohol 6, see: Xu, Y. C.; Lebeau, E.; Gillard, J. W.; Attardo, G. Tetrahedron Lett. 1993, 34, 3841.
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For the preparation of benzylic alcohol 6, see: Xu, Y. C.; Lebeau, E.; Gillard, J. W.; Attardo, G. Tetrahedron Lett. 1993, 34, 3841.
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49
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Metal salts are known to reductively decompose alkyl hydroperoxides to its corresponding alkyloxy radical. Conversely, metal salts can be oxidized by hydroperoxides and generate hydroperoxide radicals.7
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