Synthesis of 2-Boryl- and Silylindoles by Copper-Catalyzed Borylative and Silylative Cyclization of 2-Alkenylaryl Isocyanides

Mamoru Tobisu, Hirokazu Fujihara, Keika Koh and Naoto Chatani
J. Org. Chem., Article ASAP
DOI: 10.1021/jo101024f
Publication Date (Web): June 17, 2010

^o^: This type of sequence signifies an interesting methodology that has the potential to lead to a versatile intermediate (a boron / silicon handle) that will provide further entries into other biological significant compounds. The peculiar behaviour of the isocyanide makes it a nice synthon in the area of ring synthesis. In a sub-conscious level, we can indeed draw parallels from some nice Sawamura-type chemistry[1].

by Ed Law
17/06/2010

Reference:
[1] For some recent work by Sawamura, see: (a) Org. Lett., 2010, 12 (10), pp 2438–2440; (b) J. Am. Chem. Soc., 2010, 132 (17), pp 5990–5992