Synthesis of Allenyl Sulfones via a TBHP/TBAI-Mediated Reaction of Propargyl Alcohols with Sulfonyl Hydrazides.
A new TBHP/TBAI-mediated reaction of propargyl alcohols with sulfonyl hydrazides in the presence of HOAc has been established, in which a wide variety of allenyl sulfones were obtained in moderate to excellent yields. Mechanistic studies indicate that this transformation involves HOAc-promoted sulfonohydrazide intermediate formation, sequential C-O, C-N, and N-S bond cleavage, and C-S bond formation. Significantly, this sulfonohylation proceeds in a radical process and shows highly functional group compatibility and excellent regioselectivity, with a short reaction time and inexpensive reagents.
School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou, Jiangsu, 221116, People's Republic of China.
Zheng
Z
Yang
School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou, Jiangsu, 221116, People's Republic of China.
Wen-Juan
WJ
Hao
School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou, Jiangsu, 221116, People's Republic of China.
Shu-Liang
SL
Wang
Department of Public Health, Xuzhou Medical College , Xuzhou, Jiangsu 221000, People's Republic of China.
Jin-Peng
JP
Zhang
School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou, Jiangsu, 221116, People's Republic of China.
Bo
B
Jiang
Institute of Chemistry & BioMedical Sciences, Collaborative Innovation Center of Chemistry for Life Sciences, Nanjing University , Nanjing, Jiangsu, 210093, People's Republic of China.|Department of Chemistry and Biochemistry, Texas Tech University , Lubbock, Texas 79409-1061, United States.
Guigen
G
Li
School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou, Jiangsu, 221116, People's Republic of China.
Shu-Jiang
SJ
Tu
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D006835:Hydrazones / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry
D000466:Alkadienes; D000480:Alkynes; D006835:Hydrazones; D020005:Propanols; D013450:Sulfones; C028255:propargyl alcohol