Copper(ii)-catalyzed remote sulfonylation of aminoquinolines with sodium sulfinates via radical coupling

Abstract

Copper(II)-Catalyzed Remote Sulfonylation of Aminoquinolines with SodiumSulfinates via Radical Coupling. -The efficient sulfonylation of N-(quinolin--8-yl)benzamide derivatives occurs at the C5 position generating environmentally benign byproducts by utilizing stable and safe sodium sulfinates as sulfide sources. A series of quinolinyl benzamides is successfully obtained in good yields. In particular, they are less unpleasantly odorous and more environmentally friendly than previous means. -(XIA*, C.; WANG, K.; XU, J.; WEI, Z.; SHEN, C.; DUAN, G.; ZHU, Q.; ZHANG, P.; RSC Adv. 6 (2016) 43, 37173-37179,

Radicals and Sulfur Dioxide: A Versatile Combination for the Construction of Sulfonyl‐Containing Molecules

“…They described a copper-catalyzed remote CÀHb ond sulfonylation of 8-aminoquinolines (49)w ith DABCO·2SO 2 and aryldiazonium tetrafluoroborates (24)( Scheme 16). [47] This transformation is based on the extensively studied remote sulfonylation of 8-aminoquinolines with sulfonyl chlorides or sulfinates [48] andt he in situ generation of sulfonyl radicals from sulfur dioxide and diazonium salts.…”

Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

“…Xia et.al., reported an interesting copper acetate-catalyzed remote sulfonylation at the C5 position of N-(quinolin-8-yl) benzamide derivatives by utilizing sodium sulnates (Scheme 164). 263 An unusual regioselective C-H sulfonylation of N-(quinolin-8-yl)benzamide derivatives with a range of sodium Notably, sodium sulnates containing electron-rich groups proved to have superior reactivity as compared to electron-poor groups, thus affording lower yields. Disappointingly, N-(naphthalen-1-yl)benzamide, N-methyl-N-(quinolin-8-yl)benzamide and quinolin-8-yl benzoate were unsuccessful at providing the sulfonylated products under the same reaction conditions.…”

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

“…[214] 5-Sulfonyl 8-benzamidoquinolines 380 were also synthesized using sodium sulfinates 379 as sulfonylation reagents and copper (II) acetate as the catalyst: the best results were achieved with Na 2 CO 3 and TBPB in acetone at 60°C (Scheme 166). [215] Replacing of sodium sulfinates with sulfonyl hydrazides and application of Cu(OAc) 2 /Ag 2 CO 3 system in 1,4-dioxane at 100°C resulted in 5-sulfonylated derivatives of 8-benzamidoquinolines too. [216] Cu(II)-mediated sulfonylation of quinolines at the 5 th position runs in the copper coordination sphere (Scheme 167).…”