- Copper-Catalyzed Vicinal Chloro-thiolation of Alkynes with Sulfonyl Chlorides
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A copper-catalyzed vicinal chloro-thiolation of alkynes with inexpensive and diversified sulfonyl chlorides RSO2Cl (R = aryl, alkyl) has been developed. This practical and scalable reaction could be used for the construction of a number of unexplored bioactive chlorothiolated alkenes. Internal alkynes could also undergo the chloro-thiolation to provide tetrasubstituted alkynes. Preliminary mechanistic investigations revealed a plausible radical process involving a sulfur-centered radical intermediate via copper-mediated homolysis of the S-Cl bond.
- Liang, Shuaishuai,Jiang, Lvqi,Yi, Wen-Bin,Wei, Jingjing
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supporting information
p. 7024 - 7028
(2018/11/21)
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- Preparation and Diels-Alder Reactivity of Several New Chalcogen-Halogen Substituted Butadienes
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Addition of halogens and pseudohalogens across one ?-bond of 1,4-dichlorobut-2-yne, followed by a 1,4-elimination, is an efficient synthesis of several new polysubstituted butadienes.If the product dienes have a sulfur or selenium substituent they are quite reactive, undergoing cycloaddition with the moderately reactive dienophile methyl vinyl ketone at 20 deg C in the presence of boron trifluoride etherate.The regiochemistry of the cycloadditions was elucidated, and the limitations of the methodology are discussed.
- Bridges, Alexander J.,Fischer, John W.
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p. 2954 - 2961
(2007/10/02)
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- A SIMPLE PREPARATION OF SEVERAL NEW 2,3- AND 1,2,3-SUBSTITUTED BUTA-1,3-DIENES FROM 1,4-DICHLOROBUTYNE
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Addition of (pseudo) halogens across the triple bond of 1,4-dichlorobut-2-yne, followed by a 1,4-elimination, provides a very simple preparation of ten novel butadienes.
- Bridges, Alexander J.,Fischer, John W.
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p. 445 - 446
(2007/10/02)
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