Palladium-catalyzed reductive cross-coupling between α-bromo carboxamides and terminal alkynes

Aliyu，Muinat A.1; Li，Bowen1; Yang，He2; Tang，Wenjun1,3

2020-11-07

10.1039/d0qo01013h

Organic Chemistry Frontiers   影响因子和分区

2052-4110

2052-4129

An efficient Pd-catalyzed reductive cross-coupling between α-bromo carboxamides and terminal alkynes was developed. Instead of affording the Sonogashira coupling products, the protocol provided a series of β,γ-alkenyl carboxamides which were subsequently subjected to catalytic hydrogenation to give the corresponding α,α-dialkyl carboxamides. A preliminary mechanistic study revealed a radical coupling process and the solvent served as the hydrogen source. The judicious selection of a base, Pd catalyst and solvent was critical for the success of the reaction.

SCI ; IC ; CCR ; EI

英语

其他

Strategic Priority Research Program of the Chinese Academy of Sciences[XDB20000000] ; CAS[QYZDY-SSW-SLH029] ; NSFC[21725205][21432007][21572246] ; [STCSM-18520712200]

Chemistry

Chemistry, Organic

WOS:000582936400021

ROYAL SOC CHEMISTRY

20204509454239

Palladium ; Catalysis ; Hydrocarbons

Precious Metals:547.1 ; Chemical Reactions:802.2 ; Organic Compounds:804.1

2-s2.0-85094886342

Scopus

1.State Key Laboratory of Bio-Organic and Natural Products Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai,345 Ling Ling Road,200032,China
2.Shenzhen Grubbs Institute,Southern University of Science and Technology,Shenzhen,518055,China
3.School of Chemistry and Material Sciences,Hangzhou Institute for Advanced Study,University of Chinese Academy of Sciences,Hangzhou,310024,China

Aliyu，Muinat A.,Li，Bowen,Yang，He,et al. Palladium-catalyzed reductive cross-coupling between α-bromo carboxamides and terminal alkynes[J]. Organic Chemistry Frontiers,2020,7(21):3505-3508.

Aliyu，Muinat A.,Li，Bowen,Yang，He,&Tang，Wenjun.(2020).Palladium-catalyzed reductive cross-coupling between α-bromo carboxamides and terminal alkynes.Organic Chemistry Frontiers,7(21),3505-3508.

Aliyu，Muinat A.,et al."Palladium-catalyzed reductive cross-coupling between α-bromo carboxamides and terminal alkynes".Organic Chemistry Frontiers 7.21(2020):3505-3508.