20235-61-4Relevant articles and documents
A 1,4-Palladium Migration/Heck Sequence with Unactivated Alkenes: Stereoselective Synthesis of Trisubstituted 1,3-Dienes
Xue, Ze-Jian,Li, Meng-Yao,Zhu, Bin-Bin,He, Zhi-Tao,Feng, Chen-Guo,Lin, Guo-Qiang
, p. 2089 - 2092 (2021)
The palladium-catalyzed cross-coupling of ortho-vinyl aromatic bromides and olefins was achieved through a controllable 1,4-palladium migration/Heck cascade protocol. The reaction represents a mild, efficient and highly stereoselective method for the synthesis of trisubstituted 1,3-dienes, especially for triaryl-substituted ones. (Figure presented.).
Catalytic amide base system generatedin situfor 1,3-diene formation from allylbenzenes and carbonyls
Shigeno, Masanori,Kajima, Akihisa,Nakaji, Kunihito,Nozawa-Kumada, Kanako,Kondo, Yoshinori
supporting information, p. 983 - 987 (2021/02/16)
The amide base generatedin situfrom tetramethylammonium fluoride and N(TMS)3catalyzes the synthesis of 1,3-diene from an allylbenzene and carbonyl compound. The system is applicable to the transformations of a variety of allylbenzenes with functional groups (halogen, methyl, phenyl, methoxy, dimethylamino, ester, and amide moieties). Acyclic and cyclic diaryl ketones, pivalophenone, pivalaldehyde, and isobutyrophenone are used as coupling partners. The role oftransβ-methyl stilbenes in product formation is also elucidated.
Carbonyl–Olefin Cross-Metathesis Through a Visible-Light-Induced 1,3-Diol Formation and Fragmentation Sequence
Pitzer, Lena,Sandfort, Frederik,Strieth-Kalthoff, Felix,Glorius, Frank
, p. 16219 - 16223 (2018/11/23)
A visible-light-mediated approach to carbonyl–olefin cross-metathesis is described. Photoinduced hole catalysis was used to promote the formation of 1,3-diols from aldehydes and styrenes, which were then readily fragmented under acidic conditions to form the cross-metathesis products. The use of 1,3-diols as intermediates, rather than the energetically more demanding oxetanes, provides a new, orthogonal mechanistic strategy for carbonyl–olefin cross-metathesis. Furthermore, this approach does not require any metals, ligands, or additives, and provides the products with high levels of E selectivity. A mechanistic rationale is provided and supported by both theoretical calculations and experiments. Additionally, a practical synthesis of a new acridinium-based photocatalyst, including full characterization, is presented.
