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Tetrahedron Letters

Volumn 25, Issue 4, 1984, Pages 429-432

New methods and reagents in organic synthesis, 40. Amination of aromatic and heteroaromatic organometallics using diphenyl phosphorazidate (DPPA)

(3) Mori, Shigehiro a Aoyama, Toyohiko a Shioiri, Takayuki a

a NAGOYA CITY UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0039072983 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)99903-9 Document Type: Article

Times cited : (29)

References (20)

1
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- For Part 39, see S. Harusawa, R. Yoneda, T. Kurihara, Y. Hamada, and T. Shioiri, Tetrahedron Lett., submitted.

2
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- (1982) Chem. Pharm. Bull. , vol.30 , pp. 3380
- Mori¹ Sakai² Aoyama³ Shioiri⁴

3
- 84918416534
- For the other application of DPPA to the preparation of silyl diazo compounds, see:
- (1983) Chem. Lett. , vol.871
- Sekiguchi¹ Ando²

4
- 84918416533
- W. Ando, H. Tanikawa, and A. Sekiguchi, Tetrahedron Lett., in press.

5
- 85004366817
- New methods and reagents in organic synthesis. 37. Trimethylsilyldiazomethane. A convenient reagent for the preparation of vinylsilanes from alkanesulfonyl chlorides.
- For a recent preparative use of trimethylsilyldiazomethane, see
- (1983) CHEMICAL & PHARMACEUTICAL BULLETIN , vol.31 , pp. 2957
- Aoyama¹ Toyama² Tamaki³ Shioiri⁴

6
- 84943847094
- Synthesen mit Diazobenzolimid
- The reaction was discovered by
- (1903) Berichte der deutschen chemischen Gesellschaft , vol.36 , pp. 909
- Dimroth¹

7
- 84980121838
- Ueber eine neue Synthese von Diazoaminoverbindungen. 4. Mittheilung über Synthesen mit Aziden
- The reaction was discovered by
- (1905) Berichte der deutschen chemischen Gesellschaft , vol.38 , pp. 670
- Dimroth¹

8
- 84943846499
- Ueber das Diazoamino-methan (Dimethyl-triazen)
- The reaction was discovered by
- (1906) Berichte der deutschen chemischen Gesellschaft , vol.39 , pp. 3905
- Dimroth¹

9
- 0012696523
- (1969) J. Org. Chem. , vol.34 , pp. 3430
- Smith¹ Rowe² Bruner³

10
- 0005108397
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 2483
- Trost¹ Pearson²

11
- 0020694866
- (1983) Tetrahedron Lett. , vol.24 , pp. 269
- Trost¹ Pearson²

12
- 0000897865
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 1054
- Trost¹ Pearson²

13
- 0000664928
- (1982) Tetrahedron Lett. , vol.23 , pp. 699
- Hassner¹ Munger² Belinka³

14
- 0001320424
- (1983) Tetrahedron Lett. , vol.24 , pp. 3795
- Reed¹ Snieckus²

15
- 0000263951
- Reports on the direct electrophilic amination of organometallics have also appeared recently see:, and references therein
- (1982) J. Org. Chem. , vol.47 , pp. 2822
- Beak¹ Kokko²

16
- 0001686327
- (1982) Tetrahedron Lett. , vol.23 , pp. 3835
- Colvin¹ Kirby² Wilson³

17
- 0001397854
- (1982) Tetrahedron Lett. , vol.23 , pp. 5399
- Boche¹ Bernheim² Schrott³

18
- 0001063716
- (1982) Tetrahedron Lett. , vol.23 , pp. 5403
- Boche¹ Schrott²

19
- 84918416532
- In the case of the lithiation followed by the amination, n-butyllithium was used in tetra hydrofuran for the ortholithiation and warming up to −20°C was not necessary for the reaction with DPPA.

20
- 84918416531
- Free amines were obtained at this stage by removal of the solvent, followed by purification of the concentrated residue.

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