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31.9.2.1.4.7 Method 7: Arenesulfonamides via Reduction of Arenesulfonyl Azides

DOI: 10.1055/sos-SD-031-00644

Shcherbakova, I.Science of Synthesis, (200731815.

Arenesulfonyl azides 140 are readily reduced by a number of reagents to arenesulfonamides 141 under mild conditions (Scheme 60).[‌168‌‌179‌] In turn, arenesulfonyl azides can be conveniently prepared from arenesulfonyl halides and sodium azide (see Section 31.9.2.1.6.1). Thus, the reduction of arenesulfonyl azides is indirect transformation of the arenesulfonyl halides into arenesulfonamides in the absence of the nucleophilic and basic ammonia reagents (cf. Section 31.9.2.1.4.5.1). Such conditions are particularly important in the synthesis of arenesulfonamides with substituents that are sensitive to basic and/or nucleophilic reagents.

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