Journal
CHEMICAL SCIENCE
Volume 11, Issue 19, Pages 4939-4947Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc02213f
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Funding
- National Natural Science Foundation of China [21772085, 21803030, 21971107]
- Fundamental Research Funds for the Central Universities
- National Thousand Young Talents Program
- Jiangsu Innovation & Entrepreneurship Talents Plan
- NSF of Jiangsu Province in China [BK20170631]
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Redox-active esters (RAEs) as alkyl radical precursors have demonstrated great advantages for C-C bond formation. A decarboxylative cross-coupling method is described to afford substituted alkynes from various carboxylic acids using copper catalysts CuCl and Cu(acac)(2). The photoexcitation of copper acetylides with electron-rich NEt3 as a ligand provides a general strategy to generate a range of alkyl radicals from RAEs of carboxylic acids, which can be readily coupled with a variety of aromatic alkynes. The scope of this cross-coupling reaction can be further expanded to aliphatic alkynes and alkynyl silanes using a catalytic amount of preformed copper-phenylacetylide. In addition, DFT calculations revealed the favorable reaction pathway and that the bidentate acetylacetonate ligand of the copper intermediate plays an important role in inhibiting the homo-coupling of the alkyne.
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