156904-24-4Relevant articles and documents
Room-temperature palladium-catalyzed allyl cross-coupling reaction with boronic acids using phosphine-free hydrazone ligands
Mino, Takashi,Kajiwara, Kenji,Shirae, Yoshiaki,Sakamoto, Masami,Fujita, Tsutomu
, p. 2711 - 2715 (2008)
Palladium-catalyzed allyl cross-coupling reaction of allylic acetates with a variety of boronic acids at room temperature using a catalytic amount of Pd(OAc)2 with phosphine-free hydrazone as a ligand gave the allylbenzene derivatives in good yields.
Aqueous protocol for allylic arylation of cinnamyl acetates with sodium tetraphenylborate using a Bedford-type palladacycle catalyst
Ghorpade, Seema Arun,Sawant, Dinesh Nanaji,Renn, Dominik,Zernickel, Anna,Du, Weiyuan,Sekar, Nagaiyan,Eppinger, J?rg
supporting information, p. 6210 - 6214 (2018/04/23)
Allylic arylation of cinnamyl acetates with sodium tetraphenylborate using 0.002 mol% of a Bedford-type palladacycle catalyst is described. The developed methodology is applicable for a wide range of cinnamyl acetates furnishing excellent yields of up to 93%. Notably all reactions proceed smoothly under mild reaction conditions in water under an air atmosphere.
A palladium NNC-pincer complex: An efficient catalyst for allylic arylation at parts per billion levels
Hamasaka, Go,Sakurai, Fumie,Uozumi, Yasuhiro
supporting information, p. 3886 - 3888 (2015/03/04)
Allylic arylation of allylic acetates by sodium tetraarylborates in the presence of ppb to ppm (molar) loadings of a palladium NNC-pincer complex catalyst in methanol at 50°C gave the corresponding arylated products in excellent yields. Total turnover numbers of up to 500 000 000 and turnover frequencies of up to 11 250 000 h-1 were achieved.
Direct olefination of benzaldehydes into 1,3-diarylpropenes via a copper-catalyzed heterodomino Knoevenagel-decarboxylation-Csp3-H activation sequence
Zhao, Yaping,Sun, Lu,Zeng, Tieqiang,Wang, Jiayi,Peng, Yanqing,Song, Gonghua
, p. 3493 - 3498 (2014/05/20)
Copper-catalyzed direct olefination of benzaldehydes into 1,3-diarylpropenes by a novel domino Knoevenagel-decarboxylation-Csp 3-H activation sequence is reported. This method provides a concise and effective route toward the synthesis of unsymmetrical 1,3-diarylpropene derivatives. the Partner Organisations 2014.
Self-assembled poly(imidazole-palladium): Highly active, reusable catalyst at parts per million to parts per billion levels
Yamada, Yoichi M. A.,Sarkar, Shaheen M.,Uozumi, Yasuhiro
supporting information; experimental part, p. 3190 - 3198 (2012/04/10)
Metalloenzymes are essential proteins with vital activity that promote high-efficiency enzymatic reactions. To ensure catalytic activity, stability, and reusability for safe, nontoxic, sustainable chemistry, and green organic synthesis, it is important to develop metalloenzyme-inspired polymer-supported metal catalysts. Here, we present a highly active, reusable, self-assembled catalyst of poly(imidazole-acrylamide) and palladium species inspired by metalloenzymes and apply our convolution methodology to the preparation of polymeric metal catalysts. Thus, a metalloenzyme-inspired polymeric imidazole Pd catalyst (MEPI-Pd) was readily prepared by the coordinative convolution of (NH4)2PdCl4 and poly[(N-vinylimidazole)-co-(N- isopropylacrylamide)5] in a methanol-water solution at 80 °C for 30 min. SEM observation revealed that MEPI-Pd has a globular-aggregated, self-assembled structure. TEM observation and XPS and EDX analyses indicated that PdCl2 and Pd(0) nanoparticles were uniformly dispersed in MEPI-Pd. MEPI-Pd was utilized for the allylic arylation/alkenylation/vinylation of allylic esters and carbonates with aryl/alkenylboronic acids, vinylboronic acid esters, and tetraaryl borates. Even 0.8-40 mol ppm Pd of MEPI-Pd efficiently promoted allylic arylation/alkenylation/vinylation in alcohol and/or water with a catalytic turnover number (TON) of 20 000-1 250 000. Furthermore, MEPI-Pd efficiently promoted the Suzuki-Miyaura reaction of a variety of inactivated aryl chlorides as well as aryl bromides and iodides in water with a TON of up to 3 570 000. MEPI-Pd was reused for the allylic arylation and Suzuki-Miyaura reaction of an aryl chloride without loss of catalytic activity.
A highly active and reusable self-assembled poly(imidazole/palladium) catalyst: Allylic arylation/alkenylation
Sarkar, Shaheen M.,Uozumi, Yasuhiro,Yamada, Yoichi M. A.
supporting information; experimental part, p. 9437 - 9441 (2011/11/06)
Gobs of globules: A polymeric imidazole/acrylamide palladium catalyst, MPPI-Pd (M=PdIICl and Pd0), was utilized for the allylic arylation/alkenylation of allylic esters with aryl/alkenylboronic acids and tetraaryl borates. Low catalyst loadings efficiently promoted the reaction with a catalytic turnover number of 20000-1250000. The catalyst can be reused without loss of catalytic activity.
