Nickel-catalyzed regio- and diastereoselective intermolecular three-component coupling of oxabicyclic alkenes with alkynes and organoboronic acids.
نویسندگان
چکیده
Reaction of oxabicyclic alkenes with alkynes and organoboronic acids in the presence of Ni(cod)(2), P(t-Bu)(3), and CsF in a binary solvent toluene-methanol (1 : 3) at 75 to 85 °C provided exo-5,6-disubstituted 7-oxanorbornene derivatives in good to excellent yields.
منابع مشابه
Palladium-catalyzed highly regio- and stereoselective addition of organoboronic acids to allenes in the presence of AcOH.
The Pd(0)-catalyzed regio- and stereoselective addition of organoboronic acids to allenes leads to stereodefined tri- or tetrasubstituted alkenes. Furthermore, this method shows high substitutent-loading capability and tolerance of various substitutents. A hydropalladation-Suzuki coupling mechanism, which may account for the regio- and stereoselectivity, is proposed.
متن کاملNovel cyclization and reductive coupling of bicyclic olefins with alkyl propiolates catalyzed by nickel complexes*
In this article, new metal-mediated cyclization and reductive coupling reactions of bicyclic olefins with alkynes are described. Oxabicyclic alkenes undergo cyclization with alkyl propiolates at 80 °C catalyzed by nickel complexes to give benzocoumarin derivatives in high yields. The reaction of bicyclic alkenes (oxaand azacyclic alkenes) with alkyl propiolates at room temperature in the presen...
متن کاملHighly regio- and stereoselective intermolecular tandem reaction to synthesize chloro-substituted 1,3-butadienes.
A palladium catalyzed highly regio- and stereoselective intermolecular tandem reaction of alkynes, CuCl(2) and alkenes by a sequence of chloropalladation/Heck reaction to produce chloro-substituted 1,3-dienes is achieved.
متن کاملNickel-catalyzed difunctionalization of allyl moieties using organoboronic acids and halides with divergent regioselectivities† †Electronic supplementary information (ESI) available. CCDC 1563066. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc03149a
Efficient difunctionalization of alkenes allows the rapid construction of molecular complexity from simple building blocks in organic synthesis. We present herein a nickel-catalyzed dicarbofunctionalization of alkenes using readily available organoboronic acids and organic halides in a three-component fashion. In particular, an unprecedented regioselectivity of the 1,3-dicarbofunctionalization ...
متن کاملNickel(0)-catalyzed intramolecular reductive coupling of alkenes and aldehydes or ketones with hydrosilanes.
A nickel(0)-catalyzed reductive coupling of aldehydes and simple alkenes with hydrosilanes has been developed. A variety of silyl-protected 1-indanol derivatives were prepared in a highly diastereoselective manner (up to >99 : 1 dr) by employing a combination of nickel(0)/N-heterocyclic carbene and triethylsilane. The present system was also applied to a reductive coupling with ketones. Prelimi...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Chemical communications
دوره 49 15 شماره
صفحات -
تاریخ انتشار 2013