1454834-24-2Relevant academic research and scientific papers
Visible light-driven conjunctive olefination
Filippini, Dario,Silvi, Mattia
, p. 66 - 70 (2021/11/12)
Carboxylic acids and aldehydes are ubiquitous in chemistry and are native functionalities in many bioactive molecules and natural products. As such, a general cross-coupling process that involves these partners would open new avenues to achieve molecular diversity. Here we report a visible-light-mediated and transition metal-free conjunctive olefination that uses an alkene ‘linchpin’ with a defined geometry to cross-couple complex molecular scaffolds that contain carboxylic acids and aldehydes. The chemistry merges two cornerstones of organic synthesis—namely, the Wittig reaction and photoredox catalysis—in a catalytic cycle that couples a radical addition process with the redox generation of a phosphonium ylide. The methodology allows the rapid structural diversification of bioactive molecules and natural products in a native form, with a high functional group tolerance, and also forges a new alkene functional group with a programmable E–Z stereochemistry. [Figure not available: see fulltext.].
Regioselective Single-Electron Tsuji-Trost Reaction of Allylic Alcohols: A Photoredox/Nickel Dual Catalytic Approach
Wang, Zheng-Jun,Zheng, Shuai,Romero, Eugénie,Matsui, Jennifer K.,Molander, Gary A.
supporting information, p. 6543 - 6547 (2019/08/26)
A radical-mediated functionalization of allyl alcohol derived partners with a variety of alkyl 1,4-dihydropyridines via photoredox/nickel dual catalysis is described. This transformation transpires with high linear and E-selectivity, avoiding the requirement of harsh conditions (e.g., strong base, elevated temperature). Additionally, using aryl sulfinate salts as radical precursors, allyl sulfones can also be obtained. Kinetic isotope effect experiments implicated oxidative addition of the nickel catalyst to the allylic electrophile as the turnover-limiting step, supporting previous computational studies.
Palladium-catalyzed intermolecular Heck reaction of alkyl halides
Zou, Yinjun,Zhou, Jianrong
supporting information, p. 3725 - 3728 (2014/04/03)
Intermolecular Heck reaction of common alkyl halides, a longstanding problem in palladium catalysis, is realized with a simple Pd/dppf catalyst. Both primary and secondary alkyl halides are suitable for coupling with aromatic olefins. Single electron transfer from (dppf)Pd0 to alkyl halide initiated the catalytic cycle and gave alkyl radicals. This journal is the Partner Organisations 2014.
Iridium-catalyzed, diastereoselective dehydrogenative silylation of terminal alkenes with (TMSO)2MeSiH
Cheng, Chen,Simmons, Eric M.,Hartwig, John F.
supporting information, p. 8984 - 8989 (2013/09/02)
Ligands' choice: The title reaction was achieved under mild conditions with low catalyst loading. The diastereoselectivity of the reaction can be controlled by choosing the appropriate ancillary ligand (see scheme; coe=cyclooctene). The silylation product
