25203-83-2Relevant articles and documents
Visible-Light-Induced, Palladium-Catalyzed 1,4-Difunctionalization of 1,3-Dienes with Bromodifluoroacetamides
Chen, Kai,Chen, Yi-Xuan,Guan, Jian-Ping,Liu, Zhi-Lin,Xiang, Hao-Yue,Xiao, Jun-An,Xie, Zhen-Zhen,Yang, Hua,Ye, Zhi-Peng,Zheng, Yu
supporting information, p. 924 - 928 (2022/02/05)
A highly modular 1,4-difunctionalization of 1,3-dienes with bromodifluoroacetamides and sulfinates/amines through a photoinduced palladium-catalyzed radical relay process is described herein. This developed protocol offers a facile and general route to ac
Nickel-Catalyzed Carboxylation of Conjugated Dienes with Carbon Dioxide and DIBAL-H for the Synthesis of β,γ-Unsaturated Carboxylic Acids
Luo, Ying,Chan, Bun,Fukuda, Tsutomu,Onodera, Gen,Kimura, Masanari
supporting information, p. 1551 - 1554 (2021/01/21)
Conjugated dienes underwent Ni-catalyst-promoted 1,2-hydrocarboxylation in a 1:1 ratio with carbon dioxide under atmospheric pressure in the presence of diisobutylaluminum hydride (DIBAL-H) to give the corresponding β,γ-unsaturated carboxylic acids, without dimerization or oligomerization of the conjugated diene.
Selective 1,2-Aminoisothiocyanation of 1,3-Dienes Under Visible-Light Photoredox Catalysis
Guo, Weisi,Wang, Qian,Zhu, Jieping
supporting information, p. 4085 - 4089 (2020/12/25)
Selective three-component 1,2-diamination of 1,3-dienes with concurrent introduction of two orthogonally protected amino groups remains unknown despite its significant synthetic potential. We report herein that reaction of conjugated dienes with N-aminopy
Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and beyond
Gevorgyan, Vladimir,Kurandina, Daria,Shing Cheung, Kelvin Pak,Yata, Tetsuji
supporting information, p. 9932 - 9937 (2020/06/27)
A photoinduced palladium-catalyzed 1,2-carbofunctionalization of conjugated dienes has been developed. This mild modular approach, which does not require employment of exogeneous photosensitizers and external oxidants, allows for efficient and highly regio- and stereoselective synthesis of a broad range of allylic amines from readily available 1,3-dienes, alkyl iodides, and amines. Employment of O- and C-nucleophiles toward oxyalkylation and dialkylation products was also demonstrated. A putative π-allyl palladium radical-polar crossover path is proposed as a key event in this three-component coupling process. The utility of this protocol is highlighted by its application for derivatization of several amine-containing drugs.
Enantioselective Synthesis of Functionalized Arenes by Nickel-Catalyzed Site-Selective Hydroarylation of 1,3-Dienes with Aryl Boronates
Marcum, Justin S.,Meek, Simon J.,Taylor, Tiffany R.
supporting information, p. 14070 - 14075 (2020/06/10)
A catalytic method for the site-selective and enantioselective synthesis of functionalized arenes by the intermolecular hydroarylation of terminal and internal 1,3-dienes with aryl pinacolato boronates is reported. The reactions are promoted by 5.0 mol %
Corrigendum: Up the Hill: Selective Double-Bond Isomerization of Terminal 1,3-Dienes towards Z-1,3-Dienes or 2Z,4E-Dienes (Angewandte Chemie International Edition, (2012), 51, 5, (1270-1273), 10.1002/anie.201107512)
Pünner, Florian,Schmidt, Anastasia,Hilt, Gerhard
, p. 17103 - 17103 (2019/11/21)
Several years ago the authors reported an isomerisation of E-1,3-dienes by a cobalt catalyst into Z-1,3-dienes in this Communication (Scheme —original scheme). Scheme (Figure presented.) Double bond isomerisation for the stereoselective generation of Z-4
Nickel(0)-Catalyzed Hydroalkylation of 1,3-Dienes with Simple Ketones
Cheng, Lei,Li, Ming-Ming,Xiao, Li-Jun,Xie, Jian-Hua,Zhou, Qi-Lin
supporting information, p. 11627 - 11630 (2018/09/21)
We developed a highly regioselective addition of 1,3-dienes with simple ketones by nickel-hydride catalyst bearing DTBM-SegPhos ligand. A wide range of aromatic and aliphatic ketones directly coupled with 1,3-dienes, providing synthetically useful γ,δ-unsaturated ketones in high yield and regioselectivity. The asymmetric version of the reaction was also realized in high enantioselectivity by using novel chiral ligand DTBM-HO-BIPHEP. The utility of this hydroalkylation was demonstrated by facile product modification and enantioselective synthesis of (R)-flobufen.
Palladium-Catalyzed Chemoselective Protodecarboxylation of Polyenoic Acids
Al-Huniti, Mohammed H.,Perez, Mark A.,Garr, Matthew K.,Croatt, Mitchell P.
supporting information, p. 7375 - 7379 (2019/01/03)
Conditions for the first palladium-catalyzed chemoselective protodecarboxylation of polyenoic acids to give the desired polyenes in good yields are presented. The reactions proceed under mild conditions using either a Pd(0) or Pd(II) catalyst and tolerate a variety of aryl and aliphatic substitutions. Unique aspects of the reaction include the requirement of phosphines, water, and a polyene adjacent to the carboxylic acid.
Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst
Adamson, Nathan J.,Hull, Ethan,Malcolmson, Steven J.
supporting information, p. 7180 - 7183 (2017/06/05)
We report a method for the catalytic, enantioselective intermolecular addition of aliphatic amines to acyclic 1,3-dienes. In most cases, reactions proceed efficiently at or below room temperature in the presence of 5 mol % of a Pd catalyst bearing a PHOX ligand, generating allylic amines in up to 97:3 er. The presence of an electron-deficient phosphine within the ligand not only leads to a more active catalyst but also is critical for achieving high site selectivity in the transformation.
Organoselenium-Catalyzed Regioselective C?H Pyridination of 1,3-Dienes and Alkenes
Liao, Lihao,Guo, Ruizhi,Zhao, Xiaodan
supporting information, p. 3201 - 3205 (2017/03/17)
An efficient approach for organoselenium-catalyzed regioselective C?H pyridination of 1,3-dienes to form pyridinium salts has been developed. This method was also successfully applied to direct C?H pyridination of alkenes. Fluoropyridinium reagents, or initially loaded pyridine derivatives, acted as pyridine sources in the pyridination reactions. The obtained pyridinium salts could be further converted under different conditions. This work is the first example of catalytic C-2 direct C?H functionalization of 1,3-dienes and the first case of organoselenium-catalyzed C?H pyridination.
