96482-08-5

Upstream product

• 2570-63-0 thallium(III) triacetate 
• 96482-05-2 1-cyclohexyl-4-methylhex-4-en-1-ol 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 2043-61-0 cyclohexanecarbaldehyde 

Relevant academic research and scientific papers

Metalloporphyrin-Based Hypercrosslinked Polymers Catalyze Hetero-Diels–Alder Reactions of Unactivated Aldehydes with Simple Dienes: A Fascinating Strategy for the Construction of Heterogeneous Catalysts

We describe a novel and intriguing strategy for the construction of efficient heterogeneous catalysts by hypercrosslinking catalyst molecules in a one-pot Friedel–Crafts alkylation reaction. The new hypercrosslinked polymers (HCPs) as porous solid catalysts exhibit the combined advantages of homogeneous and heterogeneous catalysis, owing to their high surface area, good stability, and tailoring of catalytic centers on the frameworks. Indeed, a new class of metalloporphyrin-based HCPs were successfully synthesized using modified iron(III) porphyrin complexes as building blocks, and the resulting networks were found to be excellent recyclable heterogeneous catalysts for the hetero-Diels–Alder reaction of unactivated aldehydes with 1,3-dienes. Moreover, this new strategy showed wide adaptability, and many kinds of homogeneous-like solid-based catalysts with high catalytic performance and excellent recyclability were also constructed.

Carbocation Catalysis: Oxa-Diels-Alder Reactions of Unactivated Aldehydes and Simple Dienes

The versatility of the trityl cation (TrBF4) as a highly efficient Lewis acid organocatalyst is demonstrated in the oxa-Diels-Alder reaction of various unactivated aromatic and aliphatic aldehydes and simple unactivated dienes, such as isoprene and 2,3-dimethylbutadiene. The transformation proceeds smoothly to give 3,6-dihydropyrane adducts in high to moderate yields with catalyst loadings down to 1.0 mol-% under mild reaction conditions. In contrast to most previously reported strategies, this protocol does not require substrate functional group activation, neither by electron-deficient aldehydes (2-oxo aldehydes) or electron-rich dienes (methoxy or amino-butadiene).

Cationic iron(III) porphyrin-catalyzed [4 + 2] cycloaddition of unactivated aldehydes with simple dienes

Cationic iron(III) porphyrin was found to be an efficient catalyst for the highly chemoselective hetero-Diels-Alder-type reaction of aldehydes with 1,3-dienes. The catalyzed process did not require the use of electron-deficient aldehydes such as glyoxylic acid derivatives or activated electron-rich 1,3-dienes such as Danishefsky's diene and Rawal's diene. The high functional group tolerance and robustness of the catalyst were demonstrated. Further, the potential utility of the catalyst was demonstrated by performing the cycloaddition in the presence of water and by carrying out cycloaddition of an unactivated ketone such as cyclohexanone with a diene.

Scandium(III) Perfluorooctanesulfonate [Sc(OPf)3] : A Novel Catalyst for the Hetero Diels-Alder Reaction of Aldehydes with Non-Activated Dienes

Scandium(III) perfluorooctanesulfonate [scandium(III) perflate, Sc(OPf)3] was prepared from either scandium(III) chloride or oxide and perfluorooctanesulfonic acid. The perflate thus obtained acts as a novel Lewis acid catalyst for the intermolecular hetero Diels-Alder reaction of aldehydes with non-activated dienes under mild conditions. The characteristic features of the catalyst include (i) low hygroscopicity, (ii) ease of handling, and (iii) robustness for the recycling use.

Stereocontrolled Synthesis of Tetrahydrofurans and Tetrahydropyrans Using Thallium(III)-Induced Cyclizations

Various substituted 4-alkenols undergo electrophilic cyclization with thallium(III) salts in a regio- and stereoselective manner. The organothallium intermediate is not isolated but undergoes dethallation with concomitant 1,2-oxygen migration, leading to