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 °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%).