biostudies-literatureShen FDivision of ChemistryAmerican Chemical SocietyNational Institute of General Medical SciencesNIGMS NIH HHS1554-7https://www.ebi.ac.uk/biostudies/studies/S-EPMC5080616biostudies-literatureUnknown18(7)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.Organic lettersBismuth Acetate as a Catalyst for the Sequential Protodeboronation of Di- and Triborylated Indoles.PMC5080616R01 GM0631881012883GM63188R56 GM063188Maleczka RETyagarajan SSmith MRPerera DMaligres PEKrska SWShen FfalseBismuth Acetate as a Catalyst for the Sequential Protodeboronation of Di- and Triborylated Indoles.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.2016-01-01T00:00:00Z2016 Apr2025-04-04T08:29:03.671Z2019-03-27T02:27:32ZS-EPMC50806162699861510.1021/acs.orglett.6b00356