Silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)phenyl)prop-2-yn-1-ols to (Z)-2-methylene-1-sulfonylindolin-3-ols.
A method to prepare (Z)-2-methylene-1-sulfonylindolin-3-ols efficiently that relies on silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)phenyl)prop-2-yn-1-ols is reported. The reactions proceed rapidly at room temperature with catalyst loadings as low as 1 mol % under conditions that did not require the exclusion of air or moisture. The utility of this N-heterocyclic ring-forming strategy as a synthetic tool that makes use of unsaturated alcohols was exemplified by the conversion of the (Z)-2-methylene-1-sulfonylindolin-3-ol to examples of other members of the indole family of compounds.
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
Dewi
D
Susanti
Fujiet
F
Koh
Jeffrey Antonius
JA
Kusuma
Prasath
P
Kothandaraman
Philip Wai Hong
PW
Chan
D000085:Acetates / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D018030:Silver Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
C577168:(Z)-2-methylene-1-sulfonylindolin-3-ol; C577167:1-(2-(sulfonylamino)phenyl)prop-2-yn-1-ol; D000085:Acetates; D007211:Indoles; D020005:Propanols; D018030:Silver Compounds; D013449:Sulfonamides; C103100:silver acetate