1509939-23-4Relevant academic research and scientific papers
Reciprocal-Activation Strategy for Allylic Sulfination with Unactivated Allylic Alcohols
Xie, Peizhong,Sun, Zuolian,Li, Shuangshuang,Cai, Xinying,Qiu, Ju,Fu, Weishan,Gao, Cuiqing,Wu, Shisheng,Yang, Xiaobo,Loh, Teck-Peng,Loh, Teck-Peng
supporting information, p. 4893 - 4897 (2020/06/24)
A reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols was developed. In this reaction, the hydrogen bond interaction between allylic alcohols and sulfinic acids allowed for reciprocal activation, which enabled a dehydrative cross-coupling process to occur under mild reaction conditions. This reaction worked in an environmentally friendly manner, yielding water as the only byproduct. A variety of allylic sulfones could be obtained in good to excellent yields with wide functional group tolerance. In gram scale reactions, allylic sulfones could be conveniently isolated in high yield by filtration.
Water-Promoted Dehydrative Tsuji–Trost Reaction of Non-Derivatized Allylic Alcohols with Sulfinic Acids
Yu, Jing,Chang, Xueping,Ma, Ruitian,Zhou, Qiuju,Wei, Mengmeng,Cao, Xinhua,Ma, Xiantao
supporting information, p. 7238 - 7242 (2020/10/30)
A mild, green and extra activator-free synthesis of allylic sulfones from non-derivatized allylic alcohols and sulfinic acids was developed and only the easily-available Pd(PPh3)4 was used as the catalyst. This new method could be easily scaled up to gram scale, affording the target allylic sulfones in a nearly quantitative yield with water as the sole by-product. Mechanism studies both by various NMR techniques and by theoretical calculations suggested two reaction pathways may be involved in the reaction, which are dependent on the reaction media, that is, an eight-membered ring binding species may be formed in aqueous media between allylic alcohol, sulfinic acid and water, while a six-membered ring binding species may be formed in common aprotic organic solvent between allylic alcohol and sulfinic acid. Both binding species may be accounted for the efficient activation of allylic alcohols via hydrogen bonding.
DABSO-based, three-component, one-pot sulfone synthesis
Deeming, Alex S.,Russell, Claire J.,Hennessy, Alan J.,Willis, Michael C.
supporting information, p. 150 - 153 (2014/01/23)
The addition of Grignard reagents or organolithium reagents to the SO 2-surrogate DABSO generates a diverse set of metal sulfinates, suitable for direct conversion to sulfone products. The metal sulfinates can be trapped in situ with a wide range of C-electrophiles, including alkyl, allyl, and benzyl halides, epoxides, and (hetero)aryliodoniums.
