Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π-Acid Activation, Vinyl-Gold Addition, and Redox Catalysis

Document Type

Article

Publication Date

3-17-2021

Abstract

Here we report the first example of alkyne trifunctionalization through simultaneous construction of C-C, C-O, and C-N bonds via gold catalysis. With the assistance of a γ-keto directing group, sequential gold-catalyzed alkyne hydration, vinyl-gold nucleophilic addition, and gold(III) reductive elimination were achieved in one pot. Diazonium salts were identified as both electrophiles (N source) and oxidants (C source). Vinyl-gold(III) intermediates were revealed as effective nucleophiles toward diazonium, facilitating nucleophilic addition and reductive elimination with high efficiency. The rather comprehensive reaction sequence was achieved with excellent yields (up to 95%) and broad scope (>50 examples) under mild conditions (room temperature or 40 °C).

Identifier

85103227314 (Scopus)

Publication Title

Journal of the American Chemical Society

External Full Text Location

https://doi.org/10.1021/jacs.1c01811

e-ISSN

15205126

ISSN

00027863

PubMed ID

33661619

First Page

4074

Last Page

4082

Issue

10

Volume

143

Grant

CHE-1665122

Fund Ref

National Science Foundation

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