No.141,142
Useful Fluorine-Containing Building Block
| T2547 | 2,2,2-Trifluoro-N-phenylacetimidoyl Chloride (1) |
5g |
Trifluoro-N-phenylacetimidoyl chloride (1) has been widely used as a useful fluorine-containing building block for synthesis of many compounds. The chlorine attached to the imidoyl carbon of 1 can easily be replaced by various nucleophiles such as alcohols,1) amines,2) and carbanions.3) The nucleophilic benzylation product, prepared from benzyl alchohol, is a reagent for O-benzylation.4) The glycosylation products of 1 are used as effective glycosyl donors.5) Reductive C-F and C-Cl bond cleavage reactions of 1 afford a gem-difluorinated dianion equivalent, which can give a variety of difluorinated imines.6) Trifluoromethylated vinyl metals, metal-halogen exchange products of 1, are used for the design of many synthetic compounds.7)
References
1) Reaction with O-nucleophiles
F. Xu, S. Zhang, X. Wu, Y. Liu, W. Shi, J. Wang, Org. Lett. 2006, 8. 3207[DOI].
2) Reaction with N-nucleophiles
a) K. Kadota, Y. Dan-oh, K. Uneyama, J. Org. Chem. 1996, 61, 2364[DOI]. b) J. Xiao, X. Zhang, D. Wang, C. Yuan, J. Fluorine Chem. 1999, 99, 83[DOI].
3) Reaction with C-nucleophiles
a) P. Bravo, G. Cavicchio, M. Crucianelli, A. L. Markovsky, A. Volonterio, M. Zanda, Synlett 1996, 887. b) S. Fustero, A. Navarro, B. Pina, A. Asensio, P. Bravo, M. Crucianelli, A. Volonterio, M. Zanda, J. Org. Chem. 1998, 63, 6210[DOI].
4) Preparation of benzylation reagents
Y. Okada, M. Ohtsu, M. Bando, H. Yamada, Chem. Lett. 2007, 36, 992[DOI].
5) Preparation of glycosyl donors
a) B. Yu, H. Tao, Tetrahedron Lett. 2001, 42, 2405[DOI]. b) B. Yu, H. Tao, J. Org. Chem. 2002, 67, 9099[DOI]. c) J. Liao, J. Sun, B. Yu, Tetrahedron Lett. 2008, 49, 5036[DOI].
6) Defluorinative functionalization
T. Kobayashi, T. Nakagawa, H. Amii, K. Uneyama, Org. Lett. 2003, 5, 4297[DOI].
7) Metal-halogen exchange
a) H. Watanabe, F. Yan, T. Sakai, K. Uneyama, J. Org. Chem. 1994, 59, 758[DOI]. b) H. Amii, Y. Kishikawa, K. Uneyama, Org. Lett. 2001, 3, 1109[DOI].
F. Xu, S. Zhang, X. Wu, Y. Liu, W. Shi, J. Wang, Org. Lett. 2006, 8. 3207[DOI].
2) Reaction with N-nucleophiles
a) K. Kadota, Y. Dan-oh, K. Uneyama, J. Org. Chem. 1996, 61, 2364[DOI]. b) J. Xiao, X. Zhang, D. Wang, C. Yuan, J. Fluorine Chem. 1999, 99, 83[DOI].
3) Reaction with C-nucleophiles
a) P. Bravo, G. Cavicchio, M. Crucianelli, A. L. Markovsky, A. Volonterio, M. Zanda, Synlett 1996, 887. b) S. Fustero, A. Navarro, B. Pina, A. Asensio, P. Bravo, M. Crucianelli, A. Volonterio, M. Zanda, J. Org. Chem. 1998, 63, 6210[DOI].
4) Preparation of benzylation reagents
Y. Okada, M. Ohtsu, M. Bando, H. Yamada, Chem. Lett. 2007, 36, 992[DOI].
5) Preparation of glycosyl donors
a) B. Yu, H. Tao, Tetrahedron Lett. 2001, 42, 2405[DOI]. b) B. Yu, H. Tao, J. Org. Chem. 2002, 67, 9099[DOI]. c) J. Liao, J. Sun, B. Yu, Tetrahedron Lett. 2008, 49, 5036[DOI].
6) Defluorinative functionalization
T. Kobayashi, T. Nakagawa, H. Amii, K. Uneyama, Org. Lett. 2003, 5, 4297[DOI].
7) Metal-halogen exchange
a) H. Watanabe, F. Yan, T. Sakai, K. Uneyama, J. Org. Chem. 1994, 59, 758[DOI]. b) H. Amii, Y. Kishikawa, K. Uneyama, Org. Lett. 2001, 3, 1109[DOI].
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