81038-38-2Relevant academic research and scientific papers
Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature
Liu, Wenbo,Yang, Xiaobo,Gao, Yang,Li, Chao-Jun
supporting information, p. 8621 - 8627 (2017/07/06)
Despite the wide use of aryl radicals in organic synthesis, current methods to prepare them from aryl halides, carboxylic acids, boronic acids, and diazonium salts suffer from limitations. Aryl triflates, easily obtained from phenols, are promising aryl radical progenitors but remain elusive in this regard. Inspired by the single electron transfer process for aryl halides to access aryl radicals, we developed a simple and efficient protocol to convert aryl triflates to aryl radicals. Our success lies in exploiting sodium iodide as the soft electron donor assisted by light. This strategy enables the scalable synthesis of two types of important organic molecules, i.e., aryl boronates and aryl iodides, in good to high yields, with broad functional group compatibility in a transition-metal-free manner at room temperature. This protocol is anticipated to find potential applications in other aryl-radical-involved reactions by using aryl triflates as aryl radical precursors.
SmI2-mediated dimerization of indolylbutenones and synthesis of the myxobacterial natural product indiacen B
Marsch, Nils,Jones, Peter G.,Lindel, Thomas
supporting information, p. 1700 - 1706 (2016/04/10)
The synthesis and reactivity of indole derivatives substituted in the benzene section was studied. Starting materials 4- and 6-iodo-indole were conveniently prepared via the Batcho-Leimgruber route and purified by sublimation. Novel vicinally indolyl-subs
Synthetic studies toward penitrem E: Enantiocontrolled construction of B-E rings
Yoshii, Yu,Otsu, Takanori,Hosokawa, Norihiko,Takasu, Kiyosei,Okano, Kentaro,Tokuyama, Hidetoshi
supporting information, p. 1070 - 1073 (2015/02/19)
Enantiocontrolled construction of B-E rings of penitrem E was accomplished from 4-iodoindole in 13 steps with an overall yield of 1.7%. Diastereoselective Tf2NH-catalyzed (2+2)-cycloaddition between silyl enol ether and methyl acrylate furnishe
Nickel-mediated inter- and intramolecular C-S coupling of thiols and thioacetates with aryl iodides at room temperature
Xu, Xiao-Bo,Liu, Jian,Zhang, Jian-Jian,Wang, Ya-Wen,Peng, Yu
supporting information, p. 550 - 553 (2013/04/11)
A Ni(0)-catalyzed intermolecular cross-coupling of various functionalized thiols and aryl iodides has been developed and successfully extended to less explored intramolecular versions, where thioacetates could also be utilized as the strategic surrogate. Air-stable precatalysts, very mild conditions, and an easy protocol allow rapid access to medicinally useful aryl thioethers, as demonstrated in the facile synthesis of (±)-chuangxinmycin as a key step.
Enantioselective organo-SOMO cascade cycloadditions: A rapid approach to molecular complexity from simple aldehydes and olefins
Jui, Nathan T.,Lee, Esther C. Y.,MacMillan, David W. C.
supporting information; experimental part, p. 10015 - 10017 (2010/10/03)
A highly selective, radical-mediated (4 + 2) coupling reaction of aldehydes and conjugated olefins has been achieved through asymmetric SOMO-catalysis. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnishes a cation which is vulnerable to nucleophilic addition. A range of aromatic aldehydes are shown to couple with styrenes and dienes to provide cyclic products with high chemical efficiency, regioselectivity, and stereoselectivity.
A New Synthesis of Lysergic Acid
Hendrickson, James B.,Wang, Jian
, p. 3 - 5 (2007/10/03)
(Equation presented) (±)-Lysergic acid (1) has been synthesized via an economical 8-step route from 4-bromoindole and isocinchomeronic acid without the need to protect the indole during the synthesis. Initial efforts to form the simpler 3-acylindole derivatives first and then cyclize these were unsuccessful in the cyclization step.
A synthesis of arcyriacyanin A, an unsymmetrically substituted indole pigment of the slime mould by palladium catalyzed cross-coupling reaction
Murase, Masayuki,Watanabe, Kazuhiro,Kurihara, Takayuki,Tobinaga, Seisho
, p. 889 - 892 (2007/10/03)
The slime mould alkaloid of Arcyria obvelata Onsberg, arcyriacyanin A, was synthesized by the palladium catalyzed cross-coupling reaction with the indolylborate and 4-iodoindole derivatives, which provides an unsymmetrically substituted indole pigment.
New total synthesis of (±)-chuangxinmycin
Kato, Keisuke,Ono, Machiko,Akita, Hiroyuki
, p. 1805 - 1808 (2007/10/03)
(±)-4'-Iodoindolmycenate 6 was stereoselectively converted into the (±)-(2,3)-syn-2-thioacetoxy ester 16 with retention of C2-stereochemistry in (±)-6. Palladium-catalysed cyclisation of indolyl iodide and the internal C2 thiol group of the substrate (±)-17 derived from (±)-16 gave the (±)-cis methyl ester 2 of natural chuangxinmycin (1).
A CONVENIENT SYNTHETIC APPROACH TO 4-SUBSTITUTED INDOLES
Yamada, Fumio,Somei, Masanori
, p. 1173 - 1176 (2007/10/02)
A simple and practical synthetic method for 4-halogenoindoles, 4-indolecarbaldehyde, 4-cyanoindole, and 4-methoxycarbonylindole is elaborated.
