14752-66-0Relevant articles and documents
Convenient method for preparation of aryl sulfinates from arenes and DABSO as the SO2 surrogates
Wang, Tianlei,Wang, Fumin,Shen, Jinghua,Pang, Tianting,Ren, Yanfei,Wu, Botao,Zhang, Xubin
, p. 1183 - 1187 (2018)
A safe and efficient protocol for the synthesis of aryl sulfinates from arenes and 1,4-diazabicyclo[2,2,2]octane bis(sulfur dioxide) (DABSO) under mild conditions is described. Through in situ infrared spectroscopic studies, a plausible mechanism for the sulfination reaction is proposed as well.
Direct sulfonylation of BODIPY dyes with sodium sulfinates through oxidative radical hydrogen substitution at the α-position
Lv, Fan,Guo, Xing,Wu, Hao,Li, Heng,Tang, Bing,Yu, Changjiang,Hao, Erhong,Jiao, Lijuan
, p. 15577 - 15580 (2020)
An efficient and convenient protocol for the direct sulfonylation of BODIPY dyes with sodium sulfinates via a radical process is described for the first time. This transformation presented wide substrate scope and high regioselectivity, providing a series of α-sulfonylated BODIPYs. Meaningfully, the sulfonyl group, as a good leaving group, allowed the facile introduction of a variety of functionalities on the BODIPY core. Moreover, a 2,4-dinitrobenzenesulfonyl (DBS) group substituted BODIPY showed dramatically quenched fluorescence via the photoinduced electron transfer (PET) pathway, and was demonstrated as a new fluorescent probe for selective biothiol detection. This journal is
Construction of Sulfonyl Phthalides via Copper-Catalyzed Oxysulfonylation of 2-Vinylbenzoic Acids with Sodium Sulfinates
Xiong, Yan-Shi,Zhang, Bin,Yu, Yang,Weng, Jiang,Lu, Gui
, p. 13465 - 13472 (2019)
Copper-catalyzed difunctionalization of 2-vinylbenzoic acids with sodium sulfinates to construct substituted lactones has been realized. This protocol employs inexpensive CuCl2 as the catalyst, di-tert-butyl peroxide or O2 as the terminal oxidant, and readily available sodium sulfinates as sulfonylation reagents. High functional group tolerance and excellent yields were demonstrated by the efficient preparation of a wide range of γ-sulfonylated phthalides.
A three-component reaction of arynes, sodium sulfinates, and aldehydes toward 2-sulfonyl benzyl alcohol derivatives
Chen, Qian,Gao, Yang,Hu, Yifan,Huang, Yuanting,Li, Xianwei,Zhao, Xi
, p. 7066 - 7073 (2021)
A novel three-component reaction of arynes, sodium sulfinates, and aldehydes under mild reaction conditions is described. This transformation provides a direct synthetic approach to 2-sulfonyl benzyl alcohol derivatives, which could be rapidly converted to diverse arylsulfur compounds via the transformation of the corresponding hydroxyl groups. Various aryne precursors, sodium arenesulfinates, and aromatic aldehydes can be effectively converted to the desired products in 40-84% yields (29 examples).
Copper-mediated ortho C-H sulfonylation of benzoic acid derivatives with sodium sulfinates
Liu, Jidan,Yu, Lin,Zhuang, Shaobo,Gui, Qingwen,Chen, Xiang,Wang, Wenduo,Tan, Ze
, p. 6418 - 6421 (2015)
Copper-mediated direct ortho C-H bond sulfonylation of benzoic acid derivatives with sodium sulfinates was achieved by employing an 8-aminoquinoline moiety as the bidentate directing group. Various aryl sulfones were synthesized in good yields with excellent regioselectivity. This journal is
Photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sulfinates
Mulina, Olga M.,Ilovaisky, Alexey I.,Opatz, Till,Terent'ev, Alexander O.
supporting information, (2021/01/11)
A metal-free visible light photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates in moderate to high yields is described. The reaction proceeds in ethanol and uses eosin Y as a readily available photocatalyst in combination with nitrobenzene as an electron shuttle. Taking into account the number of steps involved (generation of the sulfonyl radical, its addition to the double bond, elimination of molecular nitrogen with formation of an iminyl radical, followed by its reduction and protonation) as well as the number of redox-active reaction partners involved, the selectivity of the process is quite impressive.
Electrosynthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates mediated by NH4I
Mulina, Olga M.,Doronin, Mikhail M.,Terent'ev, Alexander O.
supporting information, (2021/10/16)
A wide range of N-unsubstituted enaminosulfones were obtained via electrochemical sulfonylation of vinyl azides with sulfonyl radicals generated from sodium sulfinates. The discovery of N-unsubstituted enaminosulfones synthesis is based on a unique ability of the azido group to eliminate the N2 molecule. The process is performed under constant current conditions in an experimentally convenient undivided electrochemical cell equipped with a graphite anode and a stainless steel cathode applying NH4I both as the redox catalyst and the supporting electrolyte.
Visible-light-promotedE-selective synthesis of α-fluoro-β-arylalkenyl sulfidesviathe deoxygenation/isomerization process
Li, Yuxiu,Li, Xiangqian,Li, Xiaowei,Shi, Dayong
supporting information, p. 2152 - 2155 (2021/03/06)
Regioselective synthesis of α-fluoro-β-arylalkenyl sulfides has been established withgem-difluoroalkenes and sodium sulfinates in a transition-metal-free manner. A series of control experiments were executed to demonstrate thiol radicals and anions as the proposed intermediates. Notably, regioselectiveZ→Eisomerization was achieved under green light irradiation in the absence of a photoinitiator.
Direct α-Acylation of Alkenes via N-Heterocyclic Carbene, Sulfinate, and Photoredox Cooperative Triple Catalysis
Liu, Kun,Studer, Armido
supporting information, p. 4903 - 4909 (2021/05/04)
N-Heterocyclic carbene (NHC) catalysis has emerged as a versatile tool in modern synthetic chemistry. Further increasing the complexity, several processes have been introduced that proceed via dual catalysis, where the NHC organocatalyst operates in concert with a second catalytic moiety, significantly enlarging the reaction scope. In biological transformations, multiple catalysis is generally used to access complex natural products. Guided by that strategy, triple catalysis has been studied recently, where three different catalytic modes are merged in a single process. In this Communication, direct α-C-H acylation of various alkenes with aroyl fluorides using NHC, sulfinate, and photoredox cooperative triple catalysis is reported. The method allows the preparation of α-substituted vinyl ketones in moderate to high yields with excellent functional group tolerance. Mechanistic studies reveal that these cascades proceed through a sequential radical addition/coupling/elimination process. In contrast to known triple catalysis processes that operate via two sets of interwoven catalysis cycles, in the introduced process, all three cycles are interwoven.
Visible-Light-Driven Sulfonation of α-Trifluoromethylstyrenes: Access to Densely Functionalized CF3-Substituted Tertiary Alcohol
Chen, Yi-Xuan,Wang, Zhu-Jun,Xiao, Jun-An,Chen, Kai,Xiang, Hao-Yue,Yang, Hua
supporting information, p. 6558 - 6562 (2021/08/23)
Reported herein is a visible-light-induced sulfonation of α-trifluoromethylstyrenes with sodium sulfinates, which provides a series of α-trifluoromethyl-β-sulfonyl tertiary alcohols. This new synthetic protocol is enabled by a charge-transfer complex between oxygen and sulfinates, featuring broad substrate scope and scalability. Excellent functional group compatibility and chemoselectivity render this method suitable for sulfonation of pharmaceutically relevant molecules. In the presence of D2O, deuteriotrifluorinated products were also obtained, further demonstrating the flexibility and synthetic potentials of this strategy.
