Bronsted Acid Cocatalysis in Copper(I)-Photocatalyzed α-Amino C-H Bond Functionalization
Bronsted Acid Cocatalysis in Copper(I)-Photocatalyzed α-Amino C-H Bond Functionalization
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DOI：
10.1021/acscatal.5b02014
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发表时间：
2016-01-01
期刊：
影响因子：
12.9
通讯作者：
Bissember, Alex C.
中科院分区：
文献类型：
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作者：
Nicholls, Thomas P.;Constable, Grace E.;Bissember, Alex C.
我们已经利用了Bis（1,10-苯磺胺）铜（I）可见光光催化剂（VLP），[Cu（DAP）（2）]（+），以实现胺的直接α-C-H功能化。据我们所知，这代表了胺的氧化的第一个例子，这些例子最终被铜（i）VLP纳入合成靶标。 We have utilized this approach to rapidly prepare unprecedented octahydroisoquinolino [2, I -a] pyrrolo[3,4-dquinoline frameworks and exploited this process to synthesize a novel aglycone analogue of the natural product incargranine B. Most significantly, our studies suggest that the presence of trifluoroacetic acid (TFA) is crucial in mediating the aerobic参与催化循环的推定光激发铜（I）物种的氧化淬灭。
We have exploited a bis(1,10-phenanthroline)copper(I) visible light photocatalyst (VLP), [Cu(dap)(2)](+), to effect the direct alpha-C-H functionalization of amines. To our knowledge, this represents the first example of the oxidation of amines that are ultimately incorporated into synthetic targets by a copper(I) VLP. We have utilized this approach to rapidly prepare unprecedented octahydroisoquinolino [2, I -a] pyrrolo[3,4-dquinoline frameworks and exploited this process to synthesize a novel aglycone analogue of the natural product incargranine B. Most significantly, our studies suggest that the presence of trifluoroacetic acid (TFA) is crucial in mediating the aerobic oxidative quenching of a putative photoexcited copper(I) species involved in the catalytic cycle.