21550-04-9

Upstream product

• 76691-35-5 1-(3-fluorophenyl)butane-1,3-dione 
• 62967-77-5 C₂₀H₂₆F₂Sn 
• 141-75-3 butyryl chloride 
• 62942-25-0 (3-fluorophenyl)tri-n-butyltin 

Relevant academic research and scientific papers

Rhodium-Catalyzed Regioselective and Chemoselective Deoxygenative Reduction of 1,3-Diketones

The deoxygenative reduction of carbonyl compounds has been well established. However, most protocols developed typically require harsh reaction conditions or highly reactive/toxic reagents, and the deoxygenative reduction of 1,3-diketones is rarely explored despite their importance to synthetic chemistry and materials science. We describe here a rhodium-catalyzed regioselective and chemoselective deoxygenative reduction of 1,3-diketones under mild reaction conditions. This approach exhibited exceptionally high regioselectivity toward the aliphatic carbonyl reduction over aromatic carbonyl reduction. Moreover, the reaction showed good functional group tolerance and broad substrate scope as well as great potential in the late-stage modification and synthesis of natural products and pharmaceutical skeletons. Preliminary mechanistic studies and DFT calculations revealed that this reaction involved the deoxygenation of 1,3-diketone to α, β-unsaturated ketone and its subsequent 1,4-reduction. The noticeably lower energy barrier of the aliphatic C═O insertion into [Rh]-Bpin versus the aromatic C═O insertion was responsible for the high regioselectivity in this reduction.

Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation

The solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42-84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3-32 h to 10-70 min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.