41652-76-0Relevant academic research and scientific papers
Direct alkenylation of arylamines at the ortho-position
Satoh, Tsuyoshi,Ogino, Yumi,Nakamura, Masatomo
, p. 5785 - 5789 (2004)
Treatment of magnesium alkylidene carbenoids, which were generated from 1-chlorovinyl p-tolyl sulfoxides with isopropylmagnesium chloride at -78°C in toluene, with N-lithio arylamines gave ortho-alkenylated arylamines in moderate to good yields. The reaction was found to proceed in a highly stereospecific manner at the carbenoid carbon. This reaction offers a quite novel and direct alkenylation of arylamines at the ortho-position of the aromatic ring.
Nickel/Photo-Cocatalyzed Asymmetric Acyl-Carbamoylation of Alkenes
Fan, Pei,Lan, Yun,Zhang, Chang,Wang, Chuan
supporting information, p. 2180 - 2186 (2020/03/03)
An unprecedented asymmetric acyl-carbamoylation of pendant alkenes tethered on aryl carbamic chlorides with both aliphatic and aromatic aldehydes has been developed via the cooperative catalysis of a chiral nickel-PHOX complex and tetrabutylammonium decatungstate. This reaction represents the first example of merging hydrogen-atom-transfer photochemistry and asymmetric transition metal catalysis in difunctionalization of alkenes. Using this protocol, a variety of oxindoles bearing a challenging quaternary stereogenic center are furnished under mild conditions in highly enantioselective manner.
Electrochemical Synthesis of (Aza)indolines via Dehydrogenative [3+2] Annulation: Application to Total Synthesis of (±)-Hinckdentine A
Hou, Zhong-Wei,Yan, Hong,Song, Jin-Shuai,Xu, Hai-Chao
supporting information, p. 909 - 915 (2018/08/11)
An electrochemical synthesis of functionalized (aza)indolines through dehydrogenative [3+2] annulation of arylamines with tethered alkenes has been developed. Previous reported syntheses through similar inter- and intramolecular annulation reactions requi
Direct alkenylation of arylamines at the ortho-position with magnesium alkylidene carbenoids and some theoretical studies of the reactions
Satoh, Tsuyoshi,Ogino, Yumi,Ando, Kaori
, p. 10262 - 10276 (2007/10/03)
1-Chlorovinyl p-tolyl sulfoxides were synthesized from ketones and chloromethyl p-tolyl sulfoxide in high yields. Treatment of the sulfoxides with isopropylmagnesium chloride at -78°C in toluene gave magnesium alkylidene carbenoids (α-chloro alkenylmagnesium chlorides), which were treated with N-lithio arylamines to afford ortho-alkenylated arylamines in moderate yields. The reaction, in some cases, proceeded in a highly stereospecific manner at the carbon bearing the chlorine and the sulfinyl group. The structures of the α-chloro alkenylmagnesium chlorides and the reactivity of the N-lithio meta-substituted anilines were studied at the B3LYP and MP2 levels of theory with the 6-31(+)G* basis set. This reaction offers a quite novel and direct alkenylation of arylamines at the ortho-position of the aromatic ring.
