85029-28-3

Upstream product

• 85029-30-7 (5R,10R)-10-Iodo-1-oxa-spiro[4.5]dec-7-en-2-one 
• 501-52-0 3-Phenylpropionic acid 

Downstream Products

• 85029-29-4 4-(1,4-cyclohexadienyl)-2-butanone 
• 171894-86-3 3-Cyclohexa-1,4-dienyl-propionyl chloride 
• 851051-41-7 N-(1R,2R)-[2-(3-cyclohexa-1,4-dienyl-propylamino)-1,2-diphenyl-ethyl]-4-methyl-benzene sulphonamide 
• 87151-66-4 3-(cyclohexa-1,4-dien-1-yl)propan-1-ol 
• 76713-76-3 7-Phenylselanyl-tricyclo[4.2.2.0^1,6]deca-2,4,9-triene-7-carboxylic acid methyl ester 
• 172016-29-4 Tricyclo[4.2.2.0^1,6]deca-2,4,9-trien-7-ylamine 

Relevant academic research and scientific papers

Birch Reduction of Arenes Using Sodium Dispersion and DMI under Mild Conditions

An easy-to-handle sodium dispersion in paraffin oil (SD), in combination with inexpensive and environmentally benign 1,3- dimethyl-2-imidazolidinone (DMI) as an additive enables the Birch-type reduction of a variety of arenes with high yields, selectivity, and tolerance of functionality such as ether, alcohol, amine, amide, and carboxylic acid.

Organocatalyzed Birch Reduction Driven by Visible Light

The Birch reduction is a powerful synthetic methodology that uses solvated electrons to convert inert arenes to 1,4-cyclohexadienes - valuable intermediates for building molecular complexity. Birch reductions traditionally employ alkali metals dissolved in ammonia to produce a solvated electron for the reduction of unactivated arenes such as benzene (Ered -3.42 V vs SCE). Photoredox catalysts have been gaining popularity in highly reducing applications, but none have been reported to demonstrate reduction potentials powerful enough to reduce benzene. Here, we introduce benzo[ghi]perylene imides as new organic photoredox catalysts for Birch reductions performed at ambient temperature and driven by visible light from commercially available LEDs. Using low catalyst loadings (1 mol percent), benzene and other functionalized arenes were selectively transformed to 1,4-cyclohexadienes in moderate to good yields in a completely metal-free reaction. Mechanistic studies support that this unprecedented visible-light-induced reactivity is enabled by the ability of the organic photoredox catalyst to harness the energy from two visible-light photons to affect a single, high-energy chemical transformation.

Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry

Reductive electrosynthesis has faced long-standing challenges in applications to complex organic substrates at scale. Here, we show how decades of research in lithium-ion battery materials, electrolytes, and additives can serve as an inspiration for achieving practically scalable reductive electrosynthetic conditions for the Birch reduction. Specifically, we demonstrate that using a sacrificial anode material (magnesium or aluminum), combined with a cheap, nontoxic, and water-soluble proton source (dimethylurea), and an overcharge protectant inspired by battery technology [tris(pyrrolidino)phosphoramide] can allow for multigram-scale synthesis of pharmaceutically relevant building blocks. We show how these conditions have a very high level of functional-group tolerance relative to classical electrochemical and chemical dissolving-metal reductions. Finally, we demonstrate that the same electrochemical conditions can be applied to other dissolving metal-type reductive transformations, including McMurry couplings, reductive ketone deoxygenations, and epoxide openings.

An alternative route to tethered Ru(II) transfer hydrogenation catalysts

A new route towards a series of tethered η6-arene/Ru(II) catalysts for use in the transfer and pressure hydrogenation of ketones and aldehydes to alcohols is reported. The route proceeds through the formation of an amide from the diamine precursor, followed by reduction, rather than the direct alkylation of the diamine. This has the advantage that dialkylation of the amine is avoided during the synthesis. Through this new route, both racemic and enantiomerically-pure η6-arene/Ru(II) tethered catalysts can be prepared in high yield.

Efficient construction of bioactive: Trans-5A5B6C spirolactones via bicyclo[4.3.0] α-hydroxy ketones

An efficient, convenient short synthetic procedure for the synthesis of the intricate 5A5B6C-ring fusion topologies of tricyclic spiranoid β-hydroxybutyrolactones through lactonization of the key intermediate trans-α-hydro

COMPLEXES AND METHODS FOR THEIR PREPARATION

The invention provides methods for the preparation of ligands for complexes, methods for preparing complexes and complexes having those ligands. Also provided is the use of a complex as a catalyst in a method of synthesis.