220465-91-8Relevant articles and documents
Iridium-Catalyzed Isomerization/Cycloisomerization/Aromatization of N-Allyl-N-sulfonyl-o-(λ1-silylethynyl)aniline Derivatives to Give Substituted Indole Derivatives
Arisawa, Mitsuhiro,Matsuzaki, Tsuyoshi,Murai, Kenichi,Ohno, Shohei,Qiu, Jiawei,Sako, Makoto,Suzuki, Takeyuki,Takehara, Tsunayoshi,Tanaka, Tomoyuki
supporting information, p. 4284 - 4288 (2021/06/28)
We have developed a one-iridium-catalyst system that transforms N-allyl-N-sulfonyl-2-(silylalkynyl)aniline derivatives, which are 1,7-enynes in which both multiple bonds have a heteroatom, to the corresponding substituted indole derivatives via isomerizat
Direct Synthesis of 1-Arylprop-1-ynes with Calcium Carbide as an Acetylene Source
Gao, Lei,Li, Zheng
supporting information, p. 1580 - 1584 (2019/08/20)
A simple method is described for the synthesis of 1-arylprop-1-ynes directly from aromatic aldehyde p -tosylhydrazones by using calcium carbide as an acetylene source. The salient features of this protocol are its use of a readily available and easily handled source of acetylene, its operational simplicity, its high yield, and its broad substrate scope.
A one-pot synthesis of 2,2′-disubstituted diindolylmethanes (DIMs) via a sequential Sonogashira coupling and cycloisomerization/C3-functionalization of 2-iodoanilines
Kayet, Anirban,Singh, Vinod K.
, p. 6997 - 7007 (2017/09/01)
A Pd(ii)-Ag(i) catalyzed highly efficient synthesis of diindolylmethane has been developed. This transformation consists of a one-pot sequential Sonogashira coupling (and desilylation) followed by cycloisomerization/C3-functionalization of 2-iodoanilines.
Palladium and copper catalyzed Sonogashira decarboxylative coupling of aryl iodides and alkynyl carboxylic acids
Maaliki, Carine,Chevalier, Yoan,Thiery, Emilie,Thibonnet, Jér?me
supporting information, p. 3358 - 3362 (2016/07/11)
A mild procedure of palladium and copper catalyzed decarboxylative cross-coupling reaction of aryl halides and alkynyl carboxylic acids has been developed. Low molecular weight acids, to introduce small building blocks, were specifically used. This method
Fe(iv) alkylidenes via protonation of Fe(ii) vinyl chelates and a comparative M?ssbauer spectroscopic study
Lindley, Brian M.,Swidan, Ala'Aeddeen,Lobkovsky, Emil B.,Wolczanski, Peter T.,Adelhardt, Mario,Sutter, J?rg,Meyer, Karsten
, p. 4730 - 4736 (2015/07/27)
Treatment of cis-Me2Fe(PMe3)4 with di-1,2-(E-2-(pyridin-2-yl)vinyl)benzene ((bdvp)H2), a tetradentate ligand precursor, afforded (bdvp)Fe(PMe3)2 (1-PMe3) and 2 equiv. CH4/s
Well-Defined Noble Metal Single Sites in Zeolites as an Alternative to Catalysis by Insoluble Metal Salts
Rubio-Marqués, Paula,Rivero-Crespo, Miguel A.,Leyva-Pérez, Antonio,Corma, Avelino
supporting information, p. 11832 - 11837 (2015/09/28)
Insoluble precious metal chlorides in polymeric form (i.e., PtCl2, PdCl2, AuCl, RhCl3) are commonly used as catalysts for a plethora of organic reactions in solution. Here we show that only the minor soluble fraction of these precious metal chlorides (typically 5-30%) is catalytically active for the hydroamination, hydroalkoxylation, hydrosilylation, and cycloisomerization of alkynes and alkenes, and that the resting insoluble metal is catalytically useless. To circumvent this waste of precious metal and follow a rational design, we generate here well-dispersed Pt(II) and Pd(II) single sites on zeolite Y, with an exquisite control of the Lewis acidity, to catalyze different hydroaddition reactions to alkynes and alkenes with up to 104 catalytic cycles (at least 2 orders of magnitude superior to precious metal chlorides) and with high isolated yields (82-99%, >15 examples).
Tandem addition-cyclization of o-ethynylphenyl isothiocyanates with N nucleophiles; Difference of cyclization mode between primary and secondary amines
Kaname, Mamoru,Sashida, Haruki
body text, p. 748 - 751 (2012/03/08)
Silver triflate promotes the 6-exo-dig mode cyclization of the N-(2-ethynylphenyl)thioureas, which were easily obtained from the o-ethynylphenyl isothiocyanates and the primary amines, to provide the 2-imino-4-methylidene-1H-benzo[d][1,3]thiazines as the
Total synthesis of lavendamycin by a [2+2+2] cycloaddition
Nissen, Felix,Detert, Heiner
experimental part, p. 2845 - 2853 (2011/06/26)
The total synthesis of the bacterial-derived, pentacyclic, antitumor antibiotic lavendamycin has been achieved through a highly convergent strategy. The key step of this synthesis is a ruthenium-catalyzed [2+2+2] cycloaddition of an electron-deficient nit
Palladium-catalyzed highly regio-and stereoselective synthesis of 4-alkylidene-4 H -3,1-benzoxazines from N -Acyl-o -alkynylanilines
Saito, Takao,Ogawa, Shohei,Takei, Naoya,Kutsumura, Noriki,Otani, Takashi
scheme or table, p. 1098 - 1101 (2011/04/26)
The highly regio-and stereoselective 6-exo-dig mode cyclization of N-acyl-o-alkynylanilines producing 4-alkylidene-3,1-benzoxazines occurred unpredictably by use of a proper catalyst [Pd(OAc)2] and an effective additive (acetic acid) under suit
New synthesis of 3-substituted indoles using lithium trimethylsilyldiazomethane
Miyagi, Takashi,Hari, Yoshiyuki,Aoyama, Toyohiko
, p. 6303 - 6305 (2007/10/03)
Lithium trimethylsilyldiazomethane smoothly reacted with N-tosyl-o-acylanilines to give 3-substituted indoles in good to high yields.
