Finding the proton in a key intermediate of anti-Markovnikov alkyne hydration by a bifunctional catalyst.
The secondary structure of a bifunctional catalyst positions a crucial reactive proton in the final intermediate of anti-Markovnikov alkyne hydration to give an aldehyde. NMR coupling and isotopic labeling studies elucidate the location of this proton and its involvement in hydrogen bonding.
Grotjahn
Douglas B
DB
Department of Chemistry and Biochemistry, 5500 Campanile Drive, San Diego State University, San Diego, California 92182-1030, USA. grotjahn@chemistry.sdsu.edu
Kragulj
Elijah J
EJ
Zeinalipour-Yazdi
Constantinos D
CD
Miranda-Soto
Valentín
V
Lev
Daniel A
DA
Cooksy
Andrew L
AL
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D006860:Hydrogen Bonding; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D011522:Protons; D012428:Ruthenium / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D000447:Aldehydes; D000480:Alkynes; D009942:Organometallic Compounds; D011522:Protons; D014867:Water; D012428:Ruthenium