Carbopalladation/Suzuki Coupling Cascade for the Generation of Quaternary Centers. Access to Pyrrolo[1,2-b]isoquinolines
Fecha
2019-07-29Autor
Barbolla Cuadrado, Iratxe
Sotomayor Anduiza, María Nuria
Lete Expósito, María Esther
Metadatos
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The Journal of Organic Chemistry 84(16) : 10183-10196(2019)
Resumen
A convergent route to pyrrolo[1,2-b]isoquinolines with a quaternary center at C-10 has been
developed, that implies a sequential Pd(0)-catalyzed carbopalladation followed by cross-coupling
reaction with boronic acids. The adequate catalytic system and experimental conditions, with and
without the use of phosphane ligands, have been selected to control the chemoselectivity of the process,
allowing a 6-exo-carbopalladation to generate a quaternary center, and avoiding a direct Suzuki
coupling. A variety of electron rich and electron deficient arylboronic acids can be used providing an
efficient route to substituted pyrrolo[1,2-b]isoquinolines in moderate to good yields (up to 94%, 22
examples).