27458-65-7Relevant articles and documents
Daimon,Kumanotani
, p. 2359 (1975)
Acid- And base-switched palladium-catalyzed γ-C(sp3)-H alkylation and alkenylation of neopentylamine
Zhang, Jinquan,Zhang, Shuaizhong,Zou, Hongbin
supporting information, p. 3466 - 3471 (2021/05/31)
The functionalization of remote unactivated C(sp3)-H and the reaction selectivity are among the core pursuits for transition-metal catalytic system development. Herein, we report Pd-catalyzed γ-C(sp3)-H-selective alkylation and alkenylation with removable 7-azaindole as a directing group. Acid and base were found to be the decisive regulators for the selective alkylation and alkenylation, respectively, on the same single substrate under otherwise the same reaction conditions. Various acrylates were compatible for the formation of C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds. The alkenylation protocol could be further extended to acrylates with natural product units and α,β-unsaturated ketones. The preliminary synthetic manipulation of the alkylation and alkenylation products demonstrates the potential of this strategy for structurally diverse aliphatic chain extension and functionalization. Mechanistic experimental studies showed that the acidic and basic catalytic transformations shared the same six-membered dimer palladacycle.
Ruthenium(II) Catalysed Highly Regioselective C-3 Alkenylation of Indolizines and Pyrrolo[1,2-a]quinolines
Jadhav, Pankaj Pandit,Kahar, Nilesh Machhindra,Dawande, Sudam Ganpat
supporting information, p. 7831 - 7835 (2019/12/24)
Discovered the Ruthenium(II) catalysed highly stereo- and regioselective protocol for the oxidative C-3 alkenylation of indolizines and pyrrolo[1,2-a]quinolines. The methodology represents the first example for the directing group assisted C–C bond formation reaction of the indolizines. Under mild reaction conditions, this method provides an ample substrate scope to produce C-3 alkenyl indolizines in excellent to moderate yields. However, pyrrolo[1,2-a]quinolines underwent alkenynation at elevated temperature to furnish C-3 alkenyl derivatives. The functionalized indolizines were selectively reduced to obtain their saturated derivatives.
