SCOPUS 정보 검색 플랫폼

Organic Letters

Volumn 10, Issue 5, 2008, Pages 969-971

Silver-catalyzed benzylation and allylation reactions of tertiary and secondary alkyl halides with grignard reagents

(4) Someya, Hidenori a Ohmiya, Hirohisa a Yorimitsu, Hideki a Oshima, Koichiro a

a KYOTO UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 53149143210 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol800038a Document Type: Article

Times cited : (67)

References (34)

1
- 34250887174
- (a)Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 149.
- (1992) Org. React , vol.41 , pp. 149
- Lipshutz, B.H.¹ Sengupta, S.²

2
- 35348998959
- (b)Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 12404
- Do, H.-Q.¹ Daugulis, O.²

3
- 0037620634
- (c)Terao, J.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2003, 125, 5646.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 5646
- Terao, J.¹ Ikumi, A.² Kuniyasu, H.³ Kambe, N.⁴

4
- 34250863375
- (d)Terao, J.; Todo, H.; Begum, S. A.; Kuniyasu, H.; Kambe, N. Angew. Chem., Int. Ed. 2007, 46, 2086.
- (2007) Angew. Chem., Int. Ed , vol.46 , pp. 2086
- Terao, J.¹ Todo, H.² Begum, S.A.³ Kuniyasu, H.⁴ Kambe, N.⁵

5
- 0030964143
- (e)Burns, D. H.; Miller, J. D.; Chan, H. K.; Delaney, M. O. J. Am. Chem. Soc. 1997, 119, 2125.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 2125
- Burns, D.H.¹ Miller, J.D.² Chan, H.K.³ Delaney, M.O.⁴

6
- 0034725031
- (f)Cahiez, G.; Chaboche, C; Jezequel, M. Tetrahedron 2000, 56, 2733.
- (2000) Tetrahedron , vol.56 , pp. 2733
- Cahiez, G.¹ Chaboche, C.² Jezequel, M.³

7
- 34447580117
- (g)Herber, C; Breit, B. Eur. J. Org. Chem. 2007, 3512.
- (2007) Eur. J. Org. Chem , pp. 3512
- Herber, C.¹ Breit, B.²

8
- 58149201547
- (a)Cahiez, G.; Marquais, S. Synlett 1993, 56.
- (1993) Synlett , pp. 56
- Cahiez, G.¹ Marquais, S.²

9
- 0000904429
- (b)Kang, S.-K.; Kim, J.-S.; Choi, S.-C. J. Org. Chem. 1997, 62, 4208.
- (1997) J. Org. Chem , vol.62 , pp. 4208
- Kang, S.-K.¹ Kim, J.-S.² Choi, S.-C.³

10
- 33847035555
- (c)Rueping, M.; Ieawsuwan, W. Synlett 2007, 247.
- (2007) Synlett , pp. 247
- Rueping, M.¹ Ieawsuwan, W.²

11
- 0032552149
- (a)Cahiez, G.; Avedissian, H. Tetrahedron Lett. 1998, 39, 6159.
- (1998) Tetrahedron Lett , vol.39 , pp. 6159
- Cahiez, G.¹ Avedissian, H.²

12
- 33644540458
- (b)Yorimitsu, H.; Oshima, K. Pure Appl. Chem. 2006, 78, 441.
- (2006) Pure Appl. Chem , vol.78 , pp. 441
- Yorimitsu, H.¹ Oshima, K.²

13
- 1642361256
- (a)Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004,126, 3686.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 3686
- Nakamura, M.¹ Matsuo, K.² Ito, S.³ Nakamura, E.⁴

14
- 2442655977
- (b)Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297.
- (2004) Org. Lett , vol.6 , pp. 1297
- Nagano, T.¹ Hayashi, T.²

15
- 4544294922
- (c)Fürstner, A.; Martin, R. Angew. Chem., Int. Ed. 2004, 43, 3955.
- (2004) Angew. Chem., Int. Ed , vol.43 , pp. 3955
- Fürstner, A.¹ Martin, R.²

16
- 34547873501
- (d)Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc. 2007, 129, 9844.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 9844
- Hatakeyama, T.¹ Nakamura, M.²

17
- 34447275675
- (e)Cahiez, G.; Habiak, V.; Duplais, C; Moyeux, A. Angew. Chem., Int. Ed. 2007, 46, 4364.
- (2007) Angew. Chem., Int. Ed , vol.46 , pp. 4364
- Cahiez, G.¹ Habiak, V.² Duplais, C.³ Moyeux, A.⁴

18
- 34548299141
- (f)Guérinot, A.; Reymond, S.; Cossy, J. Angew. Chem., Int. Ed. 2007, 46, 6521.
- (2007) Angew. Chem., Int. Ed , vol.46 , pp. 6521
- Guérinot, A.¹ Reymond, S.² Cossy, J.³

19
- 32144461712
- (g)Bedford, R. B.; Betham, M.; Bruce, D. W.; Danopoulos, A. A.; Frost, R. M.; Hird, M. J. Org. Chem. 2006, 71, 1104.
- (2006) J. Org. Chem , vol.71 , pp. 1104
- Bedford, R.B.¹ Betham, M.² Bruce, D.W.³ Danopoulos, A.A.⁴ Frost, R.M.⁵ Hird, M.⁶

20
- 0036643488
- Silver is an effective catalyst for the coupling reaction of alkyl Grignard reagent and alkyl halide when the alkyl groups are the same, a Kochi, J. K. J. Organomet. Chem. 2002, 653, 11
- Silver is an effective catalyst for the coupling reaction of alkyl Grignard reagent and alkyl halide when the alkyl groups are the same, (a) Kochi, J. K. J. Organomet. Chem. 2002, 653, 11.

21
- 84989564580
- (b)Tamura, M.; Kochi, J. K. Synthesis 1971, 303.
- (1971) Synthesis , pp. 303
- Tamura, M.¹ Kochi, J.K.²

22
- 26844579215
- Silver-catalyzed oxidative homocoupling reactions of Grignard reagents were reported, (a) Nagano, T.; Hayashi, T. Chem. Lett. 2005, 34, 1152.
- Silver-catalyzed oxidative homocoupling reactions of Grignard reagents were reported, (a) Nagano, T.; Hayashi, T. Chem. Lett. 2005, 34, 1152.

23
- 0006790099
- (b)Tamura, M.; Kochi, J. K. Bull. Chem. Soc. Jpn. 1972, 45, 1120.
- (1972) Bull. Chem. Soc. Jpn , vol.45 , pp. 1120
- Tamura, M.¹ Kochi, J.K.²

24
- 0037021014
- (a)Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 4137.
- (2002) Angew. Chem., Int. Ed , vol.41 , pp. 4137
- Tsuji, T.¹ Yorimitsu, H.² Oshima, K.³

25
- 9244228468
- (b)Ohmiya, H.; Tsuji, T.; Yorimitsu, H.; Oshima, K. Chem. Eur. J. 2004, 10, 5640.
- (2004) Chem. Eur. J , vol.10 , pp. 5640
- Ohmiya, H.¹ Tsuji, T.² Yorimitsu, H.³ Oshima, K.⁴

26
- 58149181951
- General procedure for Ag-catalyzed benzylation of tert-alkyl halides: Silver nitrate (0.8 mg, 0.005 mmol) was placed in a 20-mL reaction flask. Anhydrous diethyl ether (2 mL) and substrate la (117.6 mg, 0.50 mmol) were added under argon. Benzylmagnesium bromide (1.0 M diethyl ether solution, 0.65 mL, 0.65 mmol) was then added to the reaction mixture at 25°C. While the Grignard reagent was being added, the mixture turned to a black suspension. After the mixture was stirred for 3 h at 25°C, black precipitations appeared at the bottom of the reaction flask, and the supernatant solution became colorless. Then the reaction mixture was poured into a saturated ammonium chloride solution (20 mL, The products were extracted with hexane (20 mL × 3, The combined organic layer was dried over Na 2S04 and concentrated. Silica gel column purification (hexane) of the crude product provided the corresponding benzylated product 2a 107 mg
- 4 and concentrated. Silica gel column purification (hexane) of the crude product provided the corresponding benzylated product 2a (107 mg, 0.44 mmol) in 87% isolated yield.

27
- 58149191847
- The reactions in hexane, toluene, and THF resulted in lower yields (ca. 70%).
- The reactions in hexane, toluene, and THF resulted in lower yields (ca. 70%).

28
- 58149182860
- 1,2-Diphenylethane (0.12 mmol) was detected.
- 1,2-Diphenylethane (0.12 mmol) was detected.

29
- 58149184292
- The reaction was slow when performed in the presence of 0.1 mol% of silver nitrate. After 5 h, 2a was obtained in 79% yield, along with 5% of 1a and 10% of the dehydrobrominated products.
- The reaction was slow when performed in the presence of 0.1 mol% of silver nitrate. After 5 h, 2a was obtained in 79% yield, along with 5% of 1a and 10% of the dehydrobrominated products.

30
- 34447539770
- Someya, H.; Ohmiya, H.; Yorimitsu, H.; Oshima, K. Tetrahedron 2007, 63, 8609.
- (2007) Tetrahedron , vol.63 , pp. 8609
- Someya, H.¹ Ohmiya, H.² Yorimitsu, H.³ Oshima, K.⁴

31
- 33847015969
- Terao, J.; Begum, S. A.; Shinohara, Y.; Tomita, M.; Naitoh, Y.; Kambe, N. Chem. Commun. 2007, 855.
- (2007) Chem. Commun , pp. 855
- Terao, J.¹ Begum, S.A.² Shinohara, Y.³ Tomita, M.⁴ Naitoh, Y.⁵ Kambe, N.⁶

32
- 0000676096
- (a)Tamura, M.; Kochi, J. K. J. Am. Chem. Soc. 1971, 93, 1483.
- (1971) J. Am. Chem. Soc , vol.93 , pp. 1483
- Tamura, M.¹ Kochi, J.K.²

33
- 0004190075
- Academic Press: New York
- (b)Kochi, J. K. Organometallic Mechanisms and Catalysis; Academic Press: New York, 1978; p 374.
- (1978) Organometallic Mechanisms and Catalysis , pp. 374
- Kochi, J.K.¹

34
- 58149196775
- The zero-valent silver can be multi-atomic or clustered and might not be single atom
- The zero-valent silver can be multi-atomic or clustered and might not be single atom.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.