Mild Reductive Functionalization of Amides into N-Sulfonylformamidines

Paz Trillo; Tove Slagbrand; Fredrik Tinnis; Hans Adolfsson

doi:10.1002/open.201700087

Mild Reductive Functionalization of Amides into N-Sulfonylformamidines

ChemistryOpen. 2017 Jul 3;6(4):484-487. doi: 10.1002/open.201700087. eCollection 2017 Aug.

Authors

Paz Trillo¹, Tove Slagbrand¹, Fredrik Tinnis¹, Hans Adolfsson^{1

2}

Affiliations

¹ Department of Organic Chemistry Stockholm University 106 91 Stockholm Sweden.
² Department of Chemistry Umeå University 901 87 Umeå Sweden.

Abstract

The development of a protocol for the reductive functionalization of amides into N-sulfonylformamidines is reported. The one-pot procedure is based on a mild catalytic reduction of tertiary amides into the corresponding enamines by the use of Mo(CO)₆ (molybdenum hexacarbonyl) and TMDS (1,1,3,3-tetramethyldisiloxane). The formed enamines were allowed to react with sulfonyl azides to give the target compounds in moderate to good yields.

Keywords: amides; amidines; enamines; reductive functionalization; sulfonyl azides.