766-92-7Relevant articles and documents
An efficient and catalyst free methylthiolation of 4-(bromomethyl)-2H-chromen-2-ones with DMSO
Chougala, Bahubali M.,Samundeeswari,Holiyachi, Megharaja,Naik, Nirmala S.,Shastri, Lokesh A.,Sunagar, Vinay A
, p. 874 - 879 (2017)
The first simple, metal free, and efficient protocol has been established for the methylthiolation of structurally diverse 4-bromomethyl-2H-chromen-2-ones using dimethyl sulfoxide (DMSO) as methylthiolation source at higher temperature. The experimental m
Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates
Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul
supporting information, p. 5022 - 5037 (2021/05/04)
Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.
A nickel-catalyzed silylation reaction of alkyl aryl sulfoxides with silylzinc reagents
Li, Wei-Ze,Wang, Zhong-Xia
supporting information, p. 5082 - 5086 (2021/06/21)
Ni(PEt3)Cl2-catalyzed silylation of alkyl aryl sulfoxides with silylzinc reagents was carried out. This protocol allows alkyl aryl sulfoxides to convert to arylsilicon compounds under mild reaction conditions, tolerates a range of functional groups and is suitable for a wide scope of substrates.
Synthesis of benzyl sulfidesviasubstitution reaction at the sulfur of phosphinic acid thioesters
Nishiyama, Yoshitake,Hosoya, Takamitsu,Yoshida, Suguru
supporting information, p. 5771 - 5774 (2020/06/03)
An ambident electrophilicity of phosphinic acid thioesters is disclosed. Unexpected carbon-sulfur bond formation took place in the reaction between phosphinic acid thioesters and benzyl Grignard reagents. The developed method for benzyl sulfides has a wide substrate scope and was applicable for the synthesis of a drug analog.
Nucleophilic Amination and Etherification of Aryl Alkyl Thioethers
Wang, Xia,Tang, Yue,Long, Cheng-Yu,Dong, Wen-Ke,Li, Chenchen,Xu, Xinhua,Zhao, Wanxiang,Wang, Xue-Qiang
supporting information, p. 4749 - 4753 (2018/08/23)
A transition-metal-free protocol capable of synthesizing diarylated aniline derivatives is reported. This method could be further employed to prepare aryl alkyl ethers. A wide range of thioethers, anilines, as well as alcohols were tolerated thanks to the mild reaction conditions. The strength of our method was demonstrated by performing a gram-scale reaction (20 mmol) followed by conversion of the nitrile group into synthetically useful aldehyde, ketone, and carboxylic acid.
Chemoenzymatic Deracemization of Chiral Sulfoxides
Nosek, Vladimír,Mí?ek, Ji?í
supporting information, p. 9849 - 9852 (2018/07/31)
The highly enantioselective enzyme methionine sulfoxide reductase A was combined with an oxaziridine-type oxidant in a biphasic setup for the deracemization of chiral sulfoxides. Remarkably, high ee values were observed with a wide range of substrates, thus providing a practical route for the synthesis of enantiomerically pure sulfoxides.
Indium-catalyzed direct conversion of dibenzyl ethers to dibenzyl sulfides using elemental sulfur and a hydrosilane and its application to the preparation of benzyl selenides
Sakai, Norio,Takada, Koji,Katayama, Masahiro,Ogiwara, Yohei
supporting information, p. 791 - 793 (2018/06/12)
Described herein is a catalytic system composed of an indium(III) compound, a hydrosilane and an easily handled form of elemental sulfur (S8) that effectively and directly catalyzes the sulfidation of dibenzyl ethers to produce dibenzyl sulfides. This system could also be applied to selenium in a straightforward conversion to dibenzyl selenides.
B(C6F5)3-Catalyzed Deoxygenation of Sulfoxides and Amine N-Oxides with Hydrosilanes
Ding, Fangwei,Jiang, Yanqiu,Gan, Shaoyan,Bao, Robert Li-Yuan,Lin, Kaifeng,Shi, Lei
, p. 3427 - 3430 (2017/07/04)
An efficient strategy for the deoxygenation of sulfoxides and amine N-oxides by using B(C6F5)3 and hydrosilanes was developed. This method provided the corresponding aromatic and aliphatic products in good to high yields and showed good functional-group tolerance under mild conditions.
Nickel-Catalyzed Cross-Coupling Reaction of Aryl Sulfoxides with Arylzinc Reagents: When the Leaving Group is an Oxidant
Yamamoto, Keita,Otsuka, Shinya,Nogi, Keisuke,Yorimitsu, Hideki
, p. 7623 - 7628 (2017/11/14)
Nickel-catalyzed Negishi-type cross-coupling of aryl methyl sulfoxides with arylzinc reagents has been developed. By consuming the catalyst-oxidizing methanesulfenate anion through oxidative homocoupling of the arylzinc reagent, smooth catalyst turnover c
Using CS2 to Probe the Mechanistic Details of Decarboxylation of Bis(phosphinite)-Ligated Nickel Pincer Formate Complexes
Ma, Qiang-Qiang,Liu, Ting,Adhikary, Anubendu,Zhang, Jie,Krause, Jeanette A.,Guan, Hairong
, p. 4077 - 4082 (2017/01/10)
The reaction of the formate complex {2,6-(R2PO)2C6H3}Ni(OCHO) (R = tBu, 5; R = iPr, 6) with CS2 shows first-order kinetics in nickel concentration and zero-order in [CS2/su
