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Convenient Synthesis of 1 H ‐Indol‐1‐yl Boronates via Palladium(0)‐Catalyzed Borylation of Bromo‐1 H ‐indoles with ‘Pinacolborane’
Author(s) -
Stadlwieser Josef F.,
Dambaur Markus E.
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690097
Subject(s) - chemistry , borylation , palladium , catalysis , pinacol , ligand (biochemistry) , medicinal chemistry , combinatorial chemistry , organic chemistry , aryl , biochemistry , alkyl , receptor
An atom‐economic Pd 0 ‐catalyzed synthesis of a series of pinacol‐type indolylboronates 3 from the corresponding bromoindole substrates 2 and pinacolborane (pinBH) as borylating agent was elaborated. The optimal catalyst system consisted of a 1 : 2 mixture of [Pd(OAc) 2 ] and the ortho ‐substituted biphenylphosphine ligand L‐3 ( Scheme 4, Table ). Our synthetic protocol was applied to the fast, preparative‐scale synthesis of 1‐substituted indolylboronates 3a – h in the presence of different functional groups, and at a catalyst load of only 1 mol‐% of Pd.