Copper-catalyzed Sonogashira reactions: advances and perspectives since 2014

Abstract

This review summarizes the recent advances and perspectives in copper catalyzed Sonogashira reaction covering both homogeneous and heterogeneous systems.

High stereoselectivity synthesis of Z-3-methyleneisoindolin-1-ones on a Cu/ETS-10 catalyst via domino coupling–cyclization without the use of protective groups and ligands

“…Combining the discussions above and literature reports, 9 c ,22 a proposed mechanism of the Z -3-methyleneisoindolin-1-ones synthesis catalyzed by Cu/ETS-10 was depicted in Scheme 5. Firstly, the Cu I species on Cu/ETS-10 can convert dynamically (CD) into Cu II species, then phenylacetylene was dehydrogenated by the base and coordinated with Cu II sites of Cu/ETS-10 to form a metal–π-complex intermediate A .…”

Theoretical study of copper hydride complexes catalyzing terminal alkyne hydroalkylation for C(sp2)–C(sp3) bond formation

“…Copper, one of the abundant and inexpensive transition metals on Earth, presents a compelling alternative to expensive transition metals such as Pd, especially in catalyzing C-C bond cross-coupling alkylation and C-N bond cross-coupling amidation. [1][2][3][4][5][6][7] Terminal alkynes, as a common substrate, can be converted into structurally diverse alkenes and alkanes 8,9 through hydrogen functionalization reactions. In recent years, the efficient, highly selective synthesis of E-alkenes has become one of the hotspots in the field of organic chemistry research.…”

Establishing the main determinants of the environmental safety of catalytic fine chemical synthesis with catalytic cross-coupling reactions

“…[8][9][10][11] Among the recognized transformative cross-coupling reactions, the Sonogashira and Mizoroki-Heck reactions stand out for their ability to forge carbon-carbon bonds under mild conditions. [12][13][14][15][16][17][18][19][20][21] The Sonogashira reaction, first introduced by Sonogashira and Hagihara in 1975, 22 involves a joint palladium and copper catalytic cycle for the coupling of terminal alkynes with aryl or vinyl halides, offering a robust platform for aryl-alkyne linkage. Similarly, the Mizoroki-Heck reaction, pioneered by Tsutomu Mizoroki and Richard F. Heck in the early 1970s, [23][24][25][26] employs palladium-catalyzed arylation and alkenylation of olefins, facilitating the construction of complex molecular frameworks.…”