1402010-97-2Relevant academic research and scientific papers
Saturated oxygen and nitrogen heterocycles: Via oxidative coupling of alkyltrifluoroborates with alkenols, alkenoic acids and protected alkenylamines
Shikora, Jonathan M.,Um, Chanchamnan,Khoder, Zainab M.,Chemler, Sherry R.
, p. 9265 - 9269 (2019/10/22)
Saturated heterocycles are important components of many bioactive compounds. The method disclosed herein enables a general route to a range of 5-, 6- and 7-membered oxygen and nitrogen heterocycles by coupling potassium alkyltrifluoroborates with heteroat
Stereospecific cross-coupling of secondary organotrifluoroborates: Potassium 1-(benzyloxy)alkyltrifluoroborates
Molander, Gary A.,Wisniewski, Steven R.
, p. 16856 - 16868,13 (2020/09/15)
Potassium 1-(alkoxy/acyloxy)alkyltrifluoroborates have been synthesized through a copper-catalyzed diboration of aldehydes and subsequent conversion of the resulting potassium 1-(hydroxy)alkyltrifluoroborates. The palladium-catalyzed Suzuki-Miyaura reaction employing the potassium 1-(benzyloxy)alkyltrifluoroborates with aryl and heteroaryl chlorides provides access to protected secondary alcohols in high yields. The β-hydride elimination pathway is avoided through use of the benzyl protecting group, which is proposed to stabilize the diorganopalladium intermediate by coordination of the arene to the metal center. This cross-coupling is stereospecific with complete retention of stereochemistry.
