Unknown

Dataset Information

0

C-H bond functionalization via hydride transfer: direct coupling of unactivated alkynes and sp(3) C-H bonds catalyzed by platinum tetraiodide.


ABSTRACT: We report a catalytic intramolecular coupling between terminal unactivated alkynes and sp(3) C-H bonds via through-space hydride transfer (HT-cyclization of alkynes). This method enables one-step preparation of complex heterocyclic compounds by alpha-alkenylation of readily available cyclic ethers and amines. We show that PtI(4) is an effective Lewis acid catalyst for the activation of terminal alkynes for hydride attack and subsequent C-C bond formation. In addition, we have shown that the activity of neutral platinum salts (PtX(n)) can be modulated by the halide ligands. This modulation in turn allows for fine-tuning of the platinum center reactivity to match the reactivity and stability of selected substrates and products.

SUBMITTER: Vadola PA 

PROVIDER: S-EPMC2971677 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

altmetric image

Publications

C-H bond functionalization via hydride transfer: direct coupling of unactivated alkynes and sp(3) C-H bonds catalyzed by platinum tetraiodide.

Vadola Paul A PA   Sames Dalibor D  

Journal of the American Chemical Society 20091101 45


We report a catalytic intramolecular coupling between terminal unactivated alkynes and sp(3) C-H bonds via through-space hydride transfer (HT-cyclization of alkynes). This method enables one-step preparation of complex heterocyclic compounds by alpha-alkenylation of readily available cyclic ethers and amines. We show that PtI(4) is an effective Lewis acid catalyst for the activation of terminal alkynes for hydride attack and subsequent C-C bond formation. In addition, we have shown that the acti  ...[more]

Similar Datasets

| S-EPMC6908613 | biostudies-literature
| S-EPMC2954885 | biostudies-literature
| S-EPMC6972843 | biostudies-literature
| S-EPMC8448122 | biostudies-literature
| S-EPMC3413323 | biostudies-literature
| S-EPMC2762545 | biostudies-literature
| S-EPMC5369400 | biostudies-literature
| S-EPMC4167400 | biostudies-literature
| S-EPMC4931026 | biostudies-literature
| S-EPMC6457195 | biostudies-literature