41332-02-9Relevant academic research and scientific papers
Chemoselective Homologation-Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
Citarella, Andrea,Holzer, Wolfgang,Ielo, Laura,Langer, Thierry,Miele, Margherita,Pace, Vittorio,Urban, Ernst,Zehl, Martin
supporting information, p. 7629 - 7634 (2020/10/12)
The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability.
Selective activation of 1,2-dichloroethane for access to β-chloroethylarenes enabled by nickel-catalyzed suzuki-type couplings
Yang, Yi,Cai, Junjie,Luo, Gen,Tong, Xia,Su, Yumei,Jiang, Yan,Liu, Yingle,Zheng, Yubin,Zeng, Jijiao,Li, Chaolin
supporting information, p. 1130 - 1134 (2019/03/26)
The selective conversion of one inactive C(sp3)-Cl bond of 1,2-dichloroethane (DCE) into C(sp3)-C(sp2) linkages for access to β-chloroethylarenes is presented here. The key to achieve the required reactivity and chemoselectivity in this synthetic method was the utilization of nickel and combinatorial nitrogen ligands as catalytic system. Synthetic advantages of this coupling chemistry included the step-simplicities to β-chloroethylarenes, the mildness and effectiveness of coupling conditions, together with the convenience for allowing further functional group transformations of the retained homobenzylic C–Cl bonds.
Gallium-catalyzed reductive chlorination of carboxylic acids with copper(II) chloride
Sakai, Norio,Nakajima, Takumi,Yoneda, Shinichiro,Konakahara, Takeo,Ogiwara, Yohei
, p. 10619 - 10623 (2015/02/19)
Described herein is the direct chlorination of carboxylic acids using copper(II) chloride via a gallium(III)-catalyzed reduction in the presence of a hydrosiloxane. During this reductive chlorination, the counteranions of CuCl2 functioned as a chloride source.
A Practical Large-scale Synthesis of (1-Naphthyl)acetylene
Hanekamp, Jaap C.,Klusener, Peter A. A.
, p. 2677 - 2682 (2007/10/02)
1-Ethynylnaphthalene has been synthesized on a large scale with high overall yields starting from 1-bromonaphthalene.
