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Convenient Synthesis of 1H-Indol-1-yl Boronates via Palladium(0)-Catalyzed Borylation of Bromo-1H-indoles with ‘Pinacolborane’

✍ Scribed by Josef F. Stadlwieser; Markus E. Dambaur

Book ID
102253382
Publisher
John Wiley and Sons
Year
2006
Tongue
German
Weight
125 KB
Volume
89
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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.

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