Organic Letters
Letter
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with DMS/I2 or I2 to give the intermediate (II). Subsequently,
nucleophilic displacement of an iodo group by 2-phenyl-
indolizine (1a) occurs to form the intermediate (III), which
continues to react with intermediate (II) leads to the
dithiolation product 3 (Scheme 6, i). In addition, the radical
mechanism is recommended for the synthesis of monothiola-
tion product. Initially, H2O2 reacts with 2 to give RS• radical
(A), and then radical (A) addition to 1a forms the intermediate
(B). Finally, the C−H bond cleavage forms the monothiolation
product 5 (Scheme 6, ii).
In summary, we have developed an efficient transition-metal-
free regioselective strategy for the controllable construction of
mono- or dithiolation indolizines. The transformation could be
accomplished under simple and mild conditions with high
regioselectivities, which provided chemists an alternative
method for designing dithiolation or monothiolation proudcts.
Owing to its high selectivity, broad substrate scope, and high
efficiency, this cross-coupling reaction should be of high
synthetic value.
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ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
■
S
Experimental procedures and spectral data (PDF)
AUTHOR INFORMATION
Corresponding Authors
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ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
The work was financially supported by the National Natural
Science Foundation of China (21302023, 21272044), the
Innovation and Strong School Project of Guangdong
Pharmaceutical University (2015cxqx212), the Science and
Technology Planning Project of Guangdong Province
(2016A010103039, 201806040009, 201804010349), and Pro-
vincial Experimental Teaching Demonstration Center of
Chemistry & Chemical Engineering.
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