{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Yuan T"],"funding":["Division of Chemistry","National Institute of General Medical Sciences","NIGMS NIH HHS"],"pagination":["4074-4082"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC10270734"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["143(10)"],"pubmed_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)."],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π-Acid Activation, Vinyl-Gold Addition, and Redox Catalysis."],"pmcid":["PMC10270734"],"funding_grant_id":["CHE-1665122","1R01GM120240-01","R01 GM120240"],"pubmed_authors":["Yuan T","Tang Q","Zhao P","Hadler N","Chen H","Shan C","Wojtas L","Ye X","Wang J","Shi X"],"additional_accession":[]},"is_claimable":false,"name":"Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π-Acid Activation, Vinyl-Gold Addition, and Redox Catalysis.","description":"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).","dates":{"release":"2021-01-01T00:00:00Z","publication":"2021 Mar","modification":"2025-04-22T01:59:55.141Z","creation":"2025-04-05T20:13:59.91Z"},"accession":"S-EPMC10270734","cross_references":{"pubmed":["33661619"],"doi":["10.1021/jacs.1c01811"]}}