期刊
ACS CATALYSIS
卷 11, 期 16, 页码 10565-10573出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c02981
关键词
C-C bond cleavage; aminoalkynes; hypervalent iodine; nitrogen radical; photoredox catalysis
资金
- National Natural Science Foundation of China [91753126, 21622207]
- Science and Technology Commission of Shanghai Municipality [21XD1424700]
- CAS Interdisciplinary Innovation Team [JCTD-2020-16]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20020200]
A selective C(sp(3))-C(sp(3)) cleavage/alkynylation of cycloalkylamides for aminoalkyne synthesis was reported under mild photoredox catalysis. γ- and δ-Aminoalkynes with diverse alkyne and amine substituents were efficiently constructed via amidyl radicals enabled by hypervalent iodine(III) reagents. Catalytic cyclic iodine(III) BI'-OAc facilitated the single-electron oxidation and ring-opening alkynylation of cycloalkylamides.
Here, we report the selective C(sp(3))-C(sp(3)) cleavage/alkynylation of cycloalkylamides for the aminoalkyne synthesis under mild photoredox catalysis conditions. gamma- and delta-Aminoalkynes with versatile alkyne and amine substituents are efficiently constructed from cyclopropylamides and cyclobutylamides via amidyl radicals enabled by hypervalent iodine(III) reagents. The catalytic amount of cyclic iodine(III) BI'-OAc facilitated the single-electron oxidation and ring-opening alkynylation of cycloalkylamides, which were investigated by a series of mechanistic probing experiments. Various alpha-amino substitutions from the oxygen, sulfur, or carbon nucleophile trapping can be performed in gram scale, and the aminoalkyne products easily derivatize to indolizidines, presenting in versatile bioactive fused azacycles.
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