Photochemical Dual-Catalytic Synthesis of Alkynyl Sulfides
A photochemical dual-catalytic cross-coupling to form alkynyl sulfides via C(sp)?S bond formation is described. The cross-coupling of thiols and bromoalkynes is promoted by a soluble organic carbazole-based photocatalyst using continuous flow techniques. Synthesis of alkynyl sulfides bearing a wide range of electronically and sterically diverse aromatic alkynes and thiols can be achieved in good to excellent yields (50–96 %). The simple continuous flow setup also allows for short reaction times (30 min) and high reproducibility on gram scale. In addition, we report the first application of photoredox/nickel dual catalysis towards macrocyclization, as well as the first example of the incorporation of an alkynyl sulfide functional group into a macrocyclic scaffold.
Santandrea, Jeffrey,Minozzi, Clémentine,Cruché, Corentin,Collins, Shawn K.
supporting information
p. 12255 - 12259
(2017/09/06)
Synthesis of 5-ortho-carboranylsalicylaldehyde and an indolinospirobenzopyran
5-ortho-Carboranylsalicylaldehyde was prepared from 5-iodosalicylaldehyde in six steps in 18% overall yield, and also from 5-iodosalicylic acid in seven steps in 45% overall yield. The reaction of 5-ortho-carboranylsalicylaldehyde with Fischer's base gave
Lee, Seung Hwan,Kwon, Young Bum,Yoon, Cheol Min
experimental part
p. 4069 - 4078
(2009/12/24)
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