62056-38-6Relevant academic research and scientific papers
Palladacycle-Catalyzed Regioselective Heck Reaction Using Diaryliodonium Triflates and Aryl Iodides
Hou, Cheng,Lei, Lu,Liang, Cui,Mo, Dong-Liang,Wang, Zhi-Xin,Zou, Pei-Sen
supporting information, p. 663 - 667 (2022/01/28)
We describe a P-containing palladacycle-catalyzed regioselective Heck reaction of 2,3-dihydrofuran with diaryliodonium salts and aryl iodides to afford 2-aryl-2,5-dihydrofurans and 2-aryl-2,3-dihydrofurans, respectively, in good yields. Mechanistic studie
Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols
Yu, Hang,Wang, Zhong-Xia
, p. 9723 - 9731 (2021/12/01)
Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols proceeds readily under mild conditions in the presence of zinc powder and MgCl2to produce allylarenes in 25-92% yields. The reaction shows high regioselectivit
In Situ Ring-Closing Strategy for Direct Synthesis of N-Heterocyclic Carbene Nickel Complexes and Their Application in Coupling of Allylic Alcohols with Aryl Boronic Acids
Wang, Yu-Bin,Liu, Bin-Yuan,Bu, Qingqing,Dai, Bin,Liu, Ning
, p. 2930 - 2940 (2020/06/17)
A in situ ring-closing strategy was developed for the synthesis of N-heterocyclic carbene nickel complexes. The process was carried out in air, and did not require solvent purification. The resulting nickel complexes were investigated as catalysts for the coupling of allylic alcohols with aryl boronic acids. A wide range of allylic substrates and aryl acids proved to be applicable to this catalytic system. Control experiments suggest that the Ni(0) may be the true active species in the coupling reactions. (Figure presented.).
Reciprocal-Activation Strategy for Allylic Sulfination with Unactivated Allylic Alcohols
Xie, Peizhong,Sun, Zuolian,Li, Shuangshuang,Cai, Xinying,Qiu, Ju,Fu, Weishan,Gao, Cuiqing,Wu, Shisheng,Yang, Xiaobo,Loh, Teck-Peng,Loh, Teck-Peng
, p. 4893 - 4897 (2020/06/24)
A reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols was developed. In this reaction, the hydrogen bond interaction between allylic alcohols and sulfinic acids allowed for reciprocal activation, which enabled a dehydrative cross-coupling process to occur under mild reaction conditions. This reaction worked in an environmentally friendly manner, yielding water as the only byproduct. A variety of allylic sulfones could be obtained in good to excellent yields with wide functional group tolerance. In gram scale reactions, allylic sulfones could be conveniently isolated in high yield by filtration.
A photocatalyst-free photo-induced denitroalkylation of β-nitrostyrenes with 4-alkyl substituted Hantzsch esters at room temperature
Duan, Chunying,Hao, Xinyu,Jin, Kun,Li, Yaming,Wang, Jiaao,Zhang, Rong,Zhang, Siyu
, (2020/02/18)
A photocatalyst-free stereoselectively photo-induced strategy for the denitroalkylation of β-nitrostyrenes using 4-alkyl substituted Hantzsch esters as the alkyl source under xenon lamp irradiation is developed. The reaction proceeds at room temperature and affords the corresponding products in moderate to excellent yields. The oxidant di-t-butyl peroxide serves as an efficient radical initiator under irradiation of a Xenon lamp, initiating alkyl radicals from the 4-alkyl substituted Hantzsch esters.
Pd/Cu-catalyzed facile approach to stilbenes: A novel diversity of TosMIC as an aryl source
Kadari, Lingaswamy,Palakodety, Radha Krishna
supporting information, p. 1978 - 1981 (2019/07/03)
Pd/Cu-catalyzed Heck type cross-coupling reaction of p-toluenesulfonylmethyl isocyanide (TosMIC) with various styrenes to access stilbenes in DMSO solvent under mild conditions is developed. This efficient and simple approach employs TosMIC as an aryl sou
Influences of Phenyl Rings on NHC Ligands with Bicyclic Architectures
Ando, Shin,Miyata, Ryota,Matsunaga, Hirofumi,Ishizuka, Tadao
, p. 128 - 139 (2019/01/04)
In addition to phosphanes, olefins, amines, and amides, over the past two decades N-heterocyclic carbene (NHC) has emerged as a useful alternative ligand. Based on a number of derivatization studies on NHC ligands, imidazol-2-ylidene and imidazolin-2-ylidene became the standard heterocyclic form, and bulky substituents have commonly been introduced on the nitrogen(s) adjacent to carbenic carbons. Our group previously developed NHCs equipped with noncarbenic carbons with a bicyclic architecture that gives them unique steric properties that make them bulky but accessible. In this study, we synthesized a novel type of NHC ligand that possesses a bicyclo[2.2.1]heptane architecture, and we compared five derivatives using copper-catalyzed allylic arylations with aryl Grignard reagents. The regioselectivity of the substitution obviously indicates that a phenyl ring over an active site has a characteristic effect on the resultant copper catalysts when γ-substitution is the major pathway.
Cross-coupling reaction of allylic ethers with aryl Grignard reagents catalyzed by a nickel pincer complex
Hashimoto, Toru,Funatsu, Kei,Ohtani, Atsufumi,Asano, Erika,Yamaguchi, Yoshitaka
, (2019/07/10)
A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using β-aminoketonato- and β-diketiminato-based pincer-type nickel(II) complexes as catalysts. An β-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed the reaction to afford the target cross-coupled products, allylbenzene derivatives, in high yield. The regioselective reaction of a variety of substituted cinnamyl ethers proceeded to give the corresponding linear products. In contrast, α- and γ-alkyl substituted allylic ethers afforded a mixture of the linear and branched products. These results indicated that the coupling reaction proceeded via a π-allyl nickel intermediate.
Method for preparing allyl compound
-
Paragraph 0042-0048; 0112-0119, (2019/11/13)
The invention relates to a method for preparing an allyl compound, and the specific steps are as follows: (1) allyl acetate, a halogenated hydrocarbon, magnesium chips, an additive, a catalyst and a ligand are dissolved in a solvent and mixed, and a crude product is obtained after reaction; and (2) after the crude product obtained in the step (1) is subjected to separation and purification, the allyl compound is obtained. Compared with the prior art, the preparation method effectively avoids the use of a pre-formed organometallic reagent in a traditional synthetic method, and has the characteristics of convenient operation, easy availability of raw materials, low cost, greenness, environmental friendliness and high yield.
Nickel-Catalyzed Direct Coupling of Allylic Alcohols with Organoboron Reagents
Wang, Gaonan,Gan, Yi,Liu, Yuanhong
supporting information, p. 916 - 920 (2018/09/22)
The direct coupling of allylic alcohols with arylboronic acids or their derivatives catalyzed by Ni(cod)2 in the presence of a catalytic amount of base has been developed. A wide variety of allylic substrates or arylboronic acids turned out to be applicable to this catalytic system. The present method does not require the use of ligands for stabilizing the nickel catalyst in most cases or additional activators for activation of allylic alcohols.
