A non-cryogenic method for the preparation of 2-(indolyl) borates, silanes, and silanols.
2-Indolyl borates are prepared via addition of LDA to a mixture of N-Boc-indole and triisopropyl borate at 0-5 degrees C. Following acidic hydrolysis, the boronic acids are isolated by crystallization in good to excellent yield (73-99%). The method is quite general, tolerating a wide range of functional groups, and also provides access to 2-silyl derivatives (80-91%).
Vazquez
Enrique
E
Department of Process Research, Merck & Co. Inc., P.O. Box 2000, Rahway, New Jersey 07065-0900, USA. enrique_vazquez@merck.com
Davies
Ian W
IW
Payack
Joseph F
JF
D001888:Boric Acids / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry
D001888:Boric Acids; D007202:Indicators and Reagents; D007211:Indoles; D012821:Silanes; C082343:silanol