Bismuth 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 prot...

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Bibliographic Details
Published in:Organic letters 2016-04, Vol.18 (7), p.1554-1557
Main Authors: Shen, Fangyi, Tyagarajan, Sriram, Perera, Damith, Krska, Shane W, Maligres, Peter E, Smith, Milton R, Maleczka, Robert E
Format: Article
Language:English
Subjects:
Acetates - chemistry
Bismuth - chemistry
Boron Compounds - chemistry
Catalysis
Indoles - chemistry
Molecular Structure
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00356