120821-94-5Relevant articles and documents
Organocatalytic deprotonative functionalization of C(sp2)-H and C(sp3)-H bonds using in situ generated onium amide bases
Inamoto, Kiyofumi,Okawa, Hitomi,Taneda, Hiroshi,Sato, Maomi,Hirono, Yutaro,Yonemoto, Misato,Kikkawa, Shoko,Kondo, Yoshinori
supporting information, p. 9771 - 9773,3 (2020/08/31)
Onium amides, generated in situ from the combination of aminosilanes and onium fluorides (R4PF, R4NF), are employed for the first time as bases for catalytic deprotonative functionalization of C(sp 2)-H and activated C(sp
Metal-free deprotonative functionalization of heteroaromatics using organic superbase catalyst
Hirono, Yutaro,Kobayashi, Koji,Yonemoto, Misato,Kondo, Yoshinori
supporting information; experimental part, p. 7623 - 7624 (2010/12/19)
Metal-free deprotonative functionalization of heteroaromatic compounds was achieved using an organic superbase catalyst; an organosilicon additive such as trimethylsilylpropyne was employed for activating the catalytic cycle of 1,2-addition to carbonyl compounds.
In situ generation and trapping of aryllithium and arylpotassium species by halogen, sulfur, and carbon electrophiles
Popov, Ilya,Do, Hien-Quang,Daugulis, Olafs
supporting information; experimental part, p. 8309 - 8313 (2010/01/16)
(Chemical Equation Presented) A general method has been developed for in situ trapping of arylmetal intermediates by halogen, sulfur, ketone, and aldehyde electrophiles affording the functionalization of the most acidic position in arene. Pentafluorobenzene, benzothiazole, and benzoxazole can be functionalized by using K3PO4 base. For less acidic arenes, tBuOLi base is required. Arenes with DMSO pKa values of 35 or less are reactive. 2009 American Chemical Society.
Catalytic activation of silylated nucleophiles using tBu-P4 as a base
Ueno, Masahiro,Hori, Chieko,Suzawa, Koichi,Ebisawa, Masashi,Kondo, Yoshinori
, p. 1965 - 1968 (2007/10/03)
Trialkylsilyl groups play an important role as effective protecting groups in organic synthesis. Various O, N, and C nucleophilic sites can be protected by trialkylsilyl groups to control the selectivity of reactions. The nucleophilic attack of a fluoride anion on a silyl group is recognized as one of the most useful methods for desilylation. The activation of the nucleophile-silicon bond is important not only for desilylation but also for the generation of a reactive nucleophilic anion to achieve a new bond formation. The phosphazene bases developed by Schwesinger are known to be strong non-metallic organic bases. Among them, the tBu-P4 base has been used for various selective deprotonative transformations, although the ability of tBu-P4 base to activate silylated nucleophiles has not yet been shown. A novel catalytic activation of various O, N, and C nucleophile-silicon bonds using tBu-P4 base was investigated to perform nucleophilic reactions with various electrophiles. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
A new strategy for deprotonative functionalization of aromatics: Transformations with excellent chemoselectivity and unique regioselectivities using t-Bu-P4 base
Imahori, Tatsushi,Kondo, Yoshinori
, p. 8082 - 8083 (2007/10/03)
A new strategy for deprotonative functionalization of aromatics using t-Bu-P4 base has been developed, and highly chemoselective transformations have been achieved with unique regioselectivities. Copyright
PHOTO-OXIDATION OF SOME DI-2-BENZOTHIAZOLYLMETHANE DERIVATIVES
Ramos, M. Teresa,Avendano, Carmen,Elguero, Jose,Jimeno, M. Luisa
, p. 497 - 502 (2007/10/02)
We report the photo-oxidation of some di-2-benzothiazolylmethane derivatives and discuss the structure of the isolated methanols and ketones.
General Reactivity of 2-Lithiobenzothiazole to Various Electrophiles and the Use as a Formyl Anion Equivalent in the Synthesis of α-Hydroxy Carbonyl Compounds
Chikashita, Hidenori,Ishibaba, Megumi,Ori, Keiji,Itoh, Kazuyoshi
, p. 3637 - 3648 (2007/10/02)
The reaction of 2-lithiobenzothiazole with a variety of electrophiles such as aldehydes, ketones, carboxylic esters, lactones, nitriles, and amides afforded the expected addition and substitution products.Trimethylsilyl chloride readily reacted with the b