Black-light-induced radical/ionic hydroxymethylation of alkyl iodides with atmospheric CO in the presence of tetrabutylammonium borohydride.
Tin-free radical/ionic hydroxymethylation of secondary and tertiary alkyl iodides proceeded efficiently in the presence of tetrabutylammonium borohydride as the hydrogen source under atmospheric pressure of CO in conjunction with photoirradiation using black light. Two possible mechanisms were proposed, both of which involve hybrid radical/ionic processes.
Kobayashi
Shoji
S
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai 599-8531, Japan.
Kawamoto
Takuji
T
Uehara
Shohei
S
Fukuyama
Takahide
T
Ryu
Ilhyong
I
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001894:Borohydrides / Q000737:chemistry*; D002248:Carbon Monoxide / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D008027:Light; D008745:Methylation; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014001:Tin / Q000737:chemistry*
D000438:Alcohols; D001894:Borohydrides; D005609:Free Radicals; D006847:Hydrocarbons, Iodinated; D000644:Quaternary Ammonium Compounds; C550222:tetrabutylammonium borohydride; D014001:Tin; D002248:Carbon Monoxide