110823-66-0Relevant articles and documents
Allylic C–H acetoxylation of terminal alkenes over TiO2 supported palladium nanoparticles using molecular oxygen as the oxidant
Zhang, Zhenzhong,Wu, Qixun,Hashiguchi, Taishin,Ishida, Tamao,Murayama, Haruno,Tokunaga, Makoto
, p. 18 - 22 (2016)
A method for synthesizing linear allylic acetates from terminal alkenes over TiO2 supported Pd nanoparticles (NPs) has been developed, in which O2 serves as the sole oxidant. Good catalytic activity was performed when using allylbenzene as a substrate and the catalyst can be reused at least five times without activity losing. The catalytic system has a broad substrate scope including transformation of 1,3-butadiene into 1,4-diacetoxy-2-butene, which is an important industrial intermediate for production of 1,4-butanediol. In contrast to previous reports that the Pd-catalyzed allylic acetoxylation is generally promoted by PdII species, the XAFS measurements suggest that this reaction is catalyzed over Pd0 NPs. Additionally, XPS analysis of the catalyst confirms the interaction between Pd and TiO2, which probably promote the initial catalytic procedure.
Enantioselective synthesis of 3-substituted dihydrobenzofurans through iridium-catalyzed intramolecular hydroarylation
Nishimura, Takahiro,Sakamoto, Kana
supporting information, p. 684 - 690 (2021/02/06)
Intramolecular hydroarylationviaC-H activation is one of the most powerful methods to synthesize carbo- and heterocyclic compounds, whereas we still have room for developing a highly enantioselective variant of the reaction. Here we describe Ir-catalyzed enantioselective intramolecular hydroarylation ofm-allyloxyphenyl ketones. The enantioselective cyclization was efficiently catalyzed by a cationic iridium complex coordinated with a conventional chiral bisphosphine ligand to give benzofurans in high yields with high enantioselectivity. A carbonyl group of ketones functioned as an effective directing group for the C-H activation. In terms of synthetic utility, we also achieved one-pot synthesis of chiral 3-substituted dihydrobenzofurans from readily available allylic carbonates andm-hydroxyacetophenonesviasequential Pd-catalyzed allylic substitution and Ir-catalyzed intramolecular hydroarylation.
C–C Cross-Coupling Reactions of Organosilanes with Terminal Alkenes and Allylic Acetates Using PdII Catalyst Supported on Starch Coated Magnetic Nanoparticles
Patra, Debabrata,Panja, Subir,Saha, Amit
, p. 878 - 883 (2020/02/13)
Starch coated magnetic nanoparticles supported palladium catalyst has been explored to perform C–C cross coupling reactions, such as oxidative Heck coupling and Tsuji–Trost allylic coupling using organosilicon compounds as one of the coupling partners. The biopolymer coated magnetic catalyst was very easy to recover magnetically and was efficiently recycled in the subsequent batches. All the reactions were performed in air and thus the necessity of air and moisture free reaction condition is avoided. The present protocols show wide substrate scope and good yields of the products.
S,O-ligand-promoted palladium-catalyzed C–H olefination of arenes with allylic substrates
Naksomboon, Kananat,álvarez-Casao, Yolanda,Uiterweerd, Michiel,Westerveld, Nick,Maciá, Beatriz,Fernández-Ibá?ez, M. ángeles
supporting information, p. 379 - 382 (2017/12/28)
An efficient catalytic system for the C–H olefination of arenes with different allylic substrates is reported. The catalytic system is based on Pd(OAc)2 and a readily accessible bidentate S,O-ligand. The methodology shows high activity with a wide range of arenes, including bulky and, electron-rich and -poor arenes. The applicability of this catalyst is demonstrated in the late-stage functionalization of the complex molecule O-methylestrone.
Palladium-catalyzed diastereoselective synthesis of homoaldol equivalent products
Horino, Yoshikazu,Sugata, Miki,Sugita, Tetsu,Aimono, Ataru,Abe, Hitoshi
, p. 2131 - 2134 (2017/05/09)
A palladium-catalyzed reaction of easily accessible 3-(pinacolatoboryl)allyl acetates and aldehydes provides facile access to synthetically useful homoaldol equivalent products with high diastereoselectivity. The reaction presumably proceeds via allylation of aldehydes with α-acetoxy allylboronates that produced in situ by reductive elimination from allylic gem-palladium/boryl intermediates.
Access to cinnamyl derivatives from arenes and allyl esters by a biomimetic aerobic oxidative dehydrogenative coupling
Gigant, Nicolas,Baeckvall, Jan-E.
supporting information, p. 1664 - 1667 (2014/04/17)
An efficient biomimetic aerobic oxidative dehydrogenative alkenylation of arenes with allyl esters is presented. The reaction proceeds under an ambient pressure of oxygen with relatively low catalyst loading of palladium acetate, employing catalytic amounts of electron-transfer mediators (ETMs). This study represents a new environmentally friendly method for the synthesis of cinnamyl derivatives.
Sterically controlled alkylation of arenes through iridium-catalyzed C-H borylation
Robbins, Daniel W.,Hartwig, John F.
supporting information, p. 933 - 937 (2013/02/25)
Complementary chemistry: A one-pot method for the site-selective alkylation of arenes controlled by steric effects is reported. The process occurs through Ir-catalyzed C-H borylation, followed by Pd- or Ni-catalyzed coupling with alkyl electrophiles. This selectivity complements that of the typical Friedel-Crafts alkylation; meta-selective alkylation of a broad range of arenes with various electronic properties and functional groups occurs in good yield with high site selectivity. Copyright
Pd(II)-catalyzed direct olefination of arenes with allylic esters and ethers
Shang, Xiaojie,Xiong, Yun,Zhang, Yuexia,Zhang, Lei,Liu, Zhongquan
supporting information; experimental part, p. 259 - 262 (2012/03/08)
A convenient Pd(II)-catalyzed direct olefination of unactivated arenes with allylic esters and ethers via C-H activation was demonstrated. Under the typical conditions, various aryl-substituted allylic esters and ethers can be prepared. Georg Thieme Verlag Stuttgart - New York.
Pd(ii)-catalyzed decarboxylative allylation and Heck-coupling of arene carboxylates with allylic halides and esters
Wang, Jiantao,Cui, Zili,Zhang, Yuexia,Li, Huajie,Wu, Long-Min,Liu, Zhongquan
supporting information; experimental part, p. 663 - 666 (2011/03/22)
This work demonstrates an alternative method to prepare allylated arenes and aryl-substituted allylic esters via catalytic decarboxylative C-C bond formation using aromatic carboxylic acids and allylic halides and esters.
PdII-catalyzed highly selective arylation of allyl esters via C-H functionalization of unreactive arenes with retention of the traditional leaving group
Pan, Delin,Yu, Miao,Chen, Wei,Jiao, Ning
experimental part, p. 1090 - 1093 (2011/07/08)
A highly selective Fujiwara-Moritani oxidative Heck reaction of allyl esters with unreactive arenes via C - H bond activation was developed, in which -H elimination is highly chemo-, regio- and stereoselective. Moreover, even electron-deficient arenes are tolerated in this type of C - H activation. 2010 Wiley-VCH Verlag GmbH Co. KGaA, Weinheim.
