Pd(II)-Catalyzed C(sp3)–H cross-coupling of aliphatic acid derivatives containing a-H atoms with organometallic reagents

March 08, 2024

• Title:       

  Pd(II)-Catalyzed C(sp3)–H cross-coupling of aliphatic acid derivatives containing a-H atoms with organometallic reagents

• Image Source:

  Weak, bidentate chelating group assisted cross-coupling of C(sp3)-H bonds in aliphatic acid derivatives with aryltrifluoroborates

• Mark:

  Scheme 1

• Associated context:

  The only exception is the protocol of Pd(II)-catalyzed cross-coupling of C(sp3)–H bonds in aliphatic amides containing a-hydrogen atoms by using arylsilanes as the coupling partners via a Pd(II)/Pd(0) catalytic cycle (Scheme 1a). To overcome the challenging substrate scope limitation and encouraged by the pioneering works on Pd(II)-catalyzed cross-coupling of C(sp3)–H bonds in aliphatic acids or their derivatives with organoboron reagents, we envisioned to develop a weak, bidentate directing group, which might be capable of increasing the rate of C–H cleavage of aliphatic acid derivatives without the Thorpe–Ingold effect and facilitating the transmetallation in the catalytic cycle due to its weak coordination (Scheme 1b).