![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)
Palladium-Catalyzed Cascade Heck Cyclization To Access Bisindoles.
Kai Yuan1, Lina Liu1, Jiayi Chen1
1State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy , China Pharmaceutical University , Nanjing 210009 , P. R. China.
Organic Letters
|June 5, 2018
Summary
A new Heck reaction strategy intercepts palladium intermediates to efficiently synthesize bisindoles. This method simplifies the creation of complex molecules through one C-N and two C-C bond formations.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Palladium-catalyzed reactions are crucial in organic synthesis.
- Efficient synthesis of bisindoles remains a challenge.
- Cyclization reactions offer pathways to complex heterocyclic structures.
Purpose of the Study:
- To develop a novel palladium-catalyzed cyclization strategy.
- To synthesize bisindoles from o-ethynylanilines.
- To establish an efficient and operationally simple protocol.
Main Methods:
- Utilizing a Heck reaction to generate σ-alkylpalladium species.
- Intercepting these intermediates for subsequent cyclization.
- Employing palladium catalysis for the transformation.
Main Results:
- Successful synthesis of bisindoles with high efficiency.
- Demonstration of a direct and operationally simple protocol.
- Formation of one C-N bond and two C-C bonds in a single process.
Conclusions:
- The described strategy provides a fundamental platform for bisindole synthesis.
- This novel method offers an efficient route to valuable heterocyclic compounds.
- The protocol's simplicity and efficiency make it broadly applicable.
Related Concept Videos
01:24Intracellular Signaling Cascades
53.7K
Once a ligand binds to a receptor, the signal is transmitted through the membrane and into the cytoplasm. The continuation of a signal in this manner is called signal transduction. Signal transduction only occurs with cell-surface receptors, which cannot interact with most components of the cell, such as DNA. Only internal receptors can interact directly with DNA in the nucleus to initiate protein synthesis. When a ligand binds to its receptor, conformational changes occur that affect the...
53.7K
01:25Rab Cascades
3.6K
Rab GTPases act in a regulated cascade during membrane fusion, helping the lipid bilayers mix. The Rab family of proteins are active when bound to GTP, and inactive when bound to GDP. Hence, they act as guanine nucleotide-dependent molecular switches. Rab-GTP recognizes and binds to long or short-range tethering proteins to capture the target vesicle. These tethers coordinate with SNAREs on the vesicle and the target membrane to assemble the trans SNARE complex that locks the mixing bilayers.
3.6K
01:22Amplifying Signals via Enzymatic Cascade
18.6K
When a ligand binds to a cell-surface receptor, the receptor's intracellular domain changes shape, which may either activate its enzyme function or allow its binding to other molecules. The initial signal is amplified by most signal transduction pathways. This means that a single ligand molecule can activate multiple molecules of a downstream target. Proteins that relay a signal are most commonly phosphorylated at one or more sites, activating or inactivating the protein. Kinases catalyze...
18.6K
01:07MAPK Signaling Cascades
8.5K
Mitogen-activated protein kinase, or MAPK pathway, activates three sequential kinases to regulate cellular responses such as proliferation, differentiation, survival, and apoptosis. The canonical MAPK pathway starts with a mitogen or growth factor binding to an RTK. The activated RTKs stimulate Ras, which recruits Raf or MAP3 Kinase (MAPKKK), the first kinase of the MAPK signaling cascade. Raf further phosphorylates and activates MEK or MAP2 Kinases (MAPKK), which in turn phosphorylates MAP...
8.5K
01:16Cascaded Op Amps
1.1K
Operational amplifiers (op-amps) are versatile electronic components that can be interconnected in a cascade - one after another in a linear sequence. This cascading is possible due to their infinite input resistance and zero output resistance, allowing them to maintain their input-output relationships even when connected in series.
In a cascaded system, each op-amp is referred to as a stage. The output of one stage drives the input of the subsequent stage. As the input signal passes through...
In a cascaded system, each op-amp is referred to as a stage. The output of one stage drives the input of the subsequent stage. As the input signal passes through...
1.1K
01:13Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization
3.3K
Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
3.3K