122-63-4Relevant articles and documents
Zn-Mediated Fragmentation of Tertiary Alkyl Oxalates Enabling Formation of Alkylated and Arylated Quaternary Carbon Centers
Ye, Yang,Chen, Haifeng,Sessler, Jonathan L.,Gong, Hegui
, p. 820 - 824 (2019)
Zn-mediated reduction of readily accessible dialkyl oxalates derived from tertiary alcohols provides an efficient approach to C-O bond fragmentation and alkyl radical formation. With MgCl2 as the indispensable additive and Ni as the promoter, trapping the radical with activated alkenes and aryl-Ni intermediates allows for the generation of alkylated and arylated all-carbon quaternary centers.
Zinc promoted mild and efficient method for the esterification of acid chlorides with alcohols
Yadav,Reddy, Gondi Sudershan,Srinivas, Dale,Himabindu, Konuru
, p. 2337 - 2342 (1998)
The esterification of variety of acid chlorides with alcohols in the presence of zinc is described. The easy formation of t-butyl and pivaloyl esters are the additional importance of this procedure.
Metal-free radical oxidative alkoxycarbonylation and imidation of alkanes
Lu, Lijun,Cheng, Danyang,Zhan, Yuanfeng,Shi, Renyi,Chiang, Chien-Wei,Lei, Aiwen
, p. 6852 - 6855 (2017)
A metal-free radical oxidative carbonylation of alkanes is demonstrated, yielding esters and imides by means of di-tert-butylperoxide as an oxidant. Various alkanes, alcohols and amides were compatible in this system generating the desired carbonyl products in up to 86% yields. We proposed a plausible radical cross-coupling process based on the preliminary mechanistic studies.
Fully recyclable Br?nsted acid catalyst systems
Watson, Christopher B.,Kuechle, Adrianna,Bergbreiter, David E.
, p. 1266 - 1273 (2021/02/26)
Homogeneous and heterogeneous sulfonic acid catalysts are some of the most common catalysts used in organic chemistry. This work explores an alternative scheme using a fully recyclable polymeric solvent (a poly-α-olefin (PAO)) and soluble PAO-anchored polyisobutylene (PIB)-bound sulfonic acid catalysts. This PAO solvent is nonvolatile and helps to exclude water by its nonpolar nature which in turn drives reactions without the need for distillation of water, avoiding the need for excess reagents. This highly nonpolar solvent system uses polyisobutylene (PIB) bound sulfonic acid catalysts that are phase-anchored in solvents like PAO. The effectivenes of these catalysts was demonstrated by their use in esterifications, acetalizations, and multicomponent condensations. These catalysts and the PAO solvent phase show excellent recyclability in schemes where products are efficiently separated. For example, this non-volatile polymeric solvent and the PIB-bound catalyst can be recycled quantitatively when volatile products are separated and purified by distillation. In other cases, product purification can be effected by product self-separation or by extraction.
Palladium-Catalyzed Direct Dicarbonylation of Amines with Ethylene to Imides
Kuai, Chang-Sheng,Wang, Le-Cheng,Wu, Xiao-Feng,Xu, Jian-Xing
supporting information, (2022/01/04)
The selective and effective conversion of low-cost and simple bulk chemicals into high value-added products through catalytic strategy has a wide range of practical significance. Here, a palladium-catalyzed method for the direct and efficient dicarbonylation of amines with basic industrial feedstock ethylene to imide has been developed. Moderate to excellent yields of the desired imides can be produced from readily available amines in a straightforward manner.
Regioselective 2-alkylation of indoles with α-bromo esters catalyzed by Pd/P,P=O system
Li, Bowen,Tang, Wenjun,Tian, Duanshuai,Tian, Wei
, (2021/08/13)
A palladium-catalyzed 2-alkylation of indoles with α-bromo esters is developed by employing a P,P=O ligand. The method features excellent regioselectivities, mild reaction conditions, and good functional group compatibility. The employment of the P,P=O ligand as well as 4? molecular sieves were crucial for the success of the transformation. Mechanistic studies indicate the reaction proceed through a radical pathway.
A Mild, General, Metal-Free Method for Desulfurization of Thiols and Disulfides Induced by Visible-Light
Qiu, Wenting,Shi, Shuai,Li, Ruining,Lin, Xianfeng,Rao, Liangming,Sun, Zhankui
supporting information, p. 1255 - 1258 (2021/05/05)
A visible-light-induced metal-free desulfurization method for thiols and disulfides has been explored. This radical desulfurization features mild conditions, robustness, and excellent functionality compatibility. It was successfully applied not only to the desulfurization of small molecules, but also to peptides.
Efficient Enzymatic Preparation of Flavor Esters in Water
Perdomo, Igor Chiarelli,Gianolio, Stefania,Pinto, Andrea,Romano, Diego,Contente, Martina Letizia,Paradisi, Francesca,Molinari, Francesco
, p. 6517 - 6522 (2019/06/20)
A straightforward biocatalytic method for the enzymatic preparation of different flavor esters starting from primary alcohols (e.g., isoamyl, n-hexyl, geranyl, cinnamyl, 2-phenethyl, and benzyl alcohols) and naturally available ethyl esters (e.g., formate, acetate, propionate, and butyrate) was developed. The biotransformations are catalyzed by an acyltransferase from Mycobacterium smegmatis (MsAcT) and proceeded with excellent yields (80-97%) and short reaction times (30-120 min), even when high substrate concentrations (up to 0.5 M) were used. This enzymatic strategy represents an efficient alternative to the application of lipases in organic solvents and a significant improvement compared with already known methods in terms of reduced use of organic solvents, paving the way to sustainable and efficient preparation of natural flavoring agents.
Bu 4 NI-Catalyzed C-C Bond Cleavage and Oxidative Esteri??cation of Allyl Alcohols with Toluene Derivatives
Chen, Yaoyao,Cui, Yongmei,Jia, Xueshun,Li, Chengliang,Li, Jian,Sun, Mingming
, p. 3667 - 3674 (2019/09/30)
A novel oxidative esterification of 1-arylprop-2-en-1-ols with toluene derivatives catalyzed by tetrabutylammonium iodide (TBAI) is reported. The optimization of the reaction conditions illustrates that each of experiment parameters including the catalyst, solvent, and oxidant is significant for present oxidative functionalization. This metal-free protocol has a broad substrate scope including the halogen groups for further functionalization and enriches the reactivity profile of allyl alcohol and toluene derivatives. In addition, this protocol represents a new transformation of allyl alcohol involving C-C bond cleavage and C-O bond forming.
Chelation-Based Homologation by Reaction of Organometallic Reagents with O -Alkyl S -Pyridin-2-yl Thiocarbonates: Synthesis of Esters from Grignard Reagents
Hashimoto, Yoshimitsu,Mano, Koudai,Morita, Nobuyoshi,Suzuki, Tomoyuki,Tamura, Osamu,Tanaka, Kosaku,Usami, Shun
supporting information, p. 1561 - 1564 (2019/08/07)
The one-carbon homologative esterification of Grignard reagents with O- alkyl S -pyridin-2-yl thiocarbonates has been explored. This one-step synthesis of esters from Grignard reagents is the first case to involve chelation-stabilized intermediates.
