Shen F1, Tyagarajan S2, Perera D1, Krska SW2, Maligres PE2, Smith MR 3rd1, Maleczka RE Jr1.
Org Lett. 2016 Apr 1;18(7):1554-7. doi: 10.1021/acs.orglett.6b00356. Epub 2016 Mar 21.Bismuth(III) acetate is a safe, inexpensive, and selective facilitator of sequential protodeboronations, which when used in conjunction with Ir-catalyzed borylations allows access to a diversity of borylated indoles. The versatility of combining Ir-catalyzed borylations with Bi(III)-catalyzed protodeboronation is demonstrated by selectively converting 6-fluoroindole into products with Bpin groups at the 4-, 5-, 7-, 2,7-, 4,7-, 3,5-, and 2,4,7-positions and the late-stage functionalization of sumatriptan.