Direct and convenient conversion of alcohols to fluorides.
[reaction: see text] Directly mixing primary, secondary, and tertiary alcohols with nC(4)F(9)SO(2)F-NR(3)(HF)(3)-NR(3) in THF or MeCN results in convenient conversion to the corresponding fluorides in high yields. The readily available reagents are easy to handle, and the mild, almost neutral reaction conditions allow for excellent functional group compatibility. A NR(3)(HF)(3)/NR(3) ratio of </=1:2 gives the highest reactivity.
Yin
Jingjun
J
Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA. jingjun@merck.com
Zarkowsky
Devin S
DS
Thomas
David W
DW
Zhao
Matthew M
MM
Huffman
Mark A
MA
D000097:Acetonitriles / Q000737:chemistry; D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D005459:Fluorides / Q000138:chemical synthesis*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry; D015394:Molecular Structure
D000097:Acetonitriles; D000438:Alcohols; D006845:Hydrocarbons, Fluorinated; D005459:Fluorides