A Novel and Direct Alkyl Azidation of p-Alkylanisoles Using Phenyl Iodine(III) Bis(trifluoroacetate) (PIFA) and Trimethylsilyl Azide

Yasuyuki Kita; Hirofumi Tohma; Takeshi Takada; Shizue Mitoh; Shigekazu Fujita; Michiyo Gyoten

doi:10.1055/s-1994-22875

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Synlett 1994; 1994(6): 427-428
DOI: 10.1055/s-1994-22875

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A Novel and Direct Alkyl Azidation of p-Alkylanisoles Using Phenyl Iodine(III) Bis(trifluoroacetate) (PIFA) and Trimethylsilyl Azide

Yasuyuki Kita^* , Hirofumi Tohma, Takeshi Takada, Shizue Mitoh, Shigekazu Fujita, Michiyo Gyoten

^*Department of Chemistry, Faculty of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565, JAPAN

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Publication Date:
18 September 2002 (online)

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Treatment of p-alkylanisoles (1a-h) bearing benzylic protons with hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA) and trimethylsilyl azide (TMSN₃) in acetonitrile gave arylalkyl azides (3a-h) in considerable yields.