C-Propargylation Overrides O-Propargylation in Reactions of Propargyl Chloride with Primary Alcohols: Rhodium-Catalyzed Transfer Hydrogenation.
The canonical SN 2 behavior displayed by alcohols and activated alkyl halides in basic media (O-alkylation) is superseded by a pathway leading to carbinol C-alkylation under the conditions of rhodium-catalyzed transfer hydrogenation. Racemic and asymmetric propargylations are described.
University of Texas at Austin, Department of Chemistry, 105 E 24th St. (A5300), Austin, TX, 78712-1167, USA.
Tao
T
Liang
University of Texas at Austin, Department of Chemistry, 105 E 24th St. (A5300), Austin, TX, 78712-1167, USA.
Sang Kook
SK
Woo
University of Texas at Austin, Department of Chemistry, 105 E 24th St. (A5300), Austin, TX, 78712-1167, USA. mkrische@mail.utexas.edu.
Michael J
MJ
Krische
D000438:Alcohols / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*
D000438:Alcohols; D000480:Alkynes; D020005:Propanols; C000628166:propargyl chloride; D010293:Pargyline; D012238:Rhodium
alcohols; hydrogenation; reaction mechanisms; rhodium; synthetic methods