Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

In the past few years the focus on central acetylcholine receptors has shifted from compounds with affinity for muscarinic acetylcholine receptors (mAChR) to compounds with affinity for nicotinic acetylcholine receptors (nAChR). The therapeutic potential includes treatment of a variety of diseases, e.g., Alzheimer's disease, Parkinson's disease, and Tourette's syndrome. This work describes the synthesis of six novel series of potent ligands with nanomolar affinity for the alpha4beta2 nAChR subtype. Structure-activity relationship (SAR) was evaluated by the calculation of a 3D-QSAR model. 3D-QSAR analysis of the compounds using the GRID/GOLPE methodology resulted in a model of high quality (R(2) = 0.97, Q(2) = 0.81). The coefficient plots reveal that the steric interactions between the target and our compounds are of major importance for the affinity. Bulky substituents in the 6-position of the pyridine ring will reduce the affinity of the compounds, whereas bulky ring systems including a sp(3)-nitrogen will increase the affinity of the compounds.

Novel potent ligands for the central nicotinic acetylcholine receptor: synthesis, receptor binding, and 3D-QSAR analysis.

A Novel Palladium-Mediated Coupling Approach to 2,3-Disubstituted Benzo[ b ]thiophenes and Its Application to the Synthesis of Tubulin Binding Agents

Gold‐Catalyzed Halogenation of Aromatics by N‐Halosuccinimides

A Pd-catalyzed asymmetric synthesis of Si-stereogenic dibenzosiloles is developed through enantioselective C–H bond functionalization of prochiral 2-(arylsilyl)aryl triflates. High chemo- and enantioselectivities are achieved by employing a Josiphos-type ligand under mild conditions.

Palladium-Catalyzed Asymmetric Synthesis of Silicon-Stereogenic Dibenzosiloles via Enantioselective C–H Bond Functionalization

N-Bromosuccinimide in Acetonitrile: A Mild and Regiospecific Nuclear Brominating Reagent for Methoxybenzenes and Naphthalenes

Mild and regiospecific nuclear iodination of methoxybenzenes and naphthalenes with N-iodosuccinimide in acetonitrile

N-Bromosuccinimide as a Regioselective Nuclear Monobrominating Reagent for Phenols and Naphthols

Short and efficient enantioselective synthesis of cis and trans pyrrolidine-2,5 dicarboxylic acids

N-BOC-ethyl pyroglutamate 1 undergoes nucleophilic ring opening with lithium methyl p-tolyl sulfinyl anion delivering the p-tolylketosulfoxide 2. Treatment of 2 with TFA gave rise to a mixture of thioesters 3a,3b. The hydrolysis of 3b afforded (2S, 5S) pirrolidine-2,5 dicarboxylic acid 5, a constituent of the red Alga Schizymenia dubyi . Under Pummerer reaction conditions (TFAA/Pyr), 2 yielded the 5-oxo-L-pipecolic acid derivative 6.

Gema Sanz

Papers

N-Bromosuccinimide in Acetonitrile: A Mild and Regiospecific Nuclear Brominating Reagent for Methoxybenzenes and Naphthalenes

Mild and regiospecific nuclear iodination of methoxybenzenes and naphthalenes with N-iodosuccinimide in acetonitrile

N-Bromosuccinimide as a Regioselective Nuclear Monobrominating Reagent for Phenols and Naphthols

Short and efficient enantioselective synthesis of cis and trans pyrrolidine-2,5 dicarboxylic acids

Short and Efficient Enantioselective Synthesis of cis- and trans- Pyrrolidine-2,5-dicarboxylic Acids.