Microwave assisted asymmetric Suzuki-Miyaura and Negishi cross-coupling reactions: synthesis of chiral binaphthalenes

Synthesis of axially chiral biaryl compounds by asymmetric catalytic reactions with transition metals

“…Espinet et al tried to address this issue by proposing a micro-wave irradiation as an alternative to the traditional oil bath heating (Table 3.6) [97]. With this method, reaction times were dramatically improved (from 6 days to a few hours), but unfortunately where the yields were preserved, enantioselectivities were lowered.…”

“…In a subsequent paper, Espinet et al showed that the use of microwave allowed to reduce drastically the reaction times from several days to 45 min while maintaining the yields [97].…”

Carbon–Carbon Bond Forming Reactions Mediated by Organozinc Reagents

“…Cross-coupling with aryl chlorides can be achieved within minutes in high yields with very low catalyst loadings using a combination of Pd 2 (dba) 3 and PtBu 3 [139]. The same technique can be utilized in the Negishi cross-coupling catalyzed by palladium in the presence of the ligand 160 of the JosiPhos family, providing the enantioselective formation of chiral binaphthyls such as 159 (Scheme 4.36) [140].…”

“…Scheme 4.36 Pd-catalyzed cross-coupling reactions of diarylzincs with aryl bromides under microwave irradiation[140].…”

Regioselective Suzuki-Miyaura Reaction: Application to the Microwave-promoted Synthesis of 4,7-Diarylquinazolines

“…Microwave irradiation is a simple, rapid and effective method for transferring energy to a polar reaction medium [23]. Consequently, microwave irradiation has been widely applied in organic synthesis, including C-C cross-coupling reactions [24,25].…”