期刊
ACS CATALYSIS
卷 10, 期 1, 页码 435-440出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b04592
关键词
C-H activation; ruthenium; meta selectivity; remote functionalization; late-stage diversification; DFT; purines
资金
- DAAD
- DFG (Gottfried-Wilhelm-Leibniz prize)
The full control of site selectivity in C-H activation is paramount for the programmed late-stage functionalization of structurally complex structures. During the past decade, directing groups have revolutionized molecular synthesis in terms of ortho-selective C-H activation. In sharp contrast, a selectivity switch that guides the typical ortho- to remote meta-C-H activation has thus far proven elusive. Herein, we describe the realization of such a concept for a robust selectivity control in ruthenium catalysis. The distal C-H transformation was guided by key mechanistic insights into the mild, synergistic action of carboxylates and phosphines in ruthenium(II) catalysis. Our findings allowed remote selectivity in broadly effective late-stage diversification of structurally complex drugs and natural product molecules, tolerating sensitive fluorescent dyes, drugs, lipids, peptides, nucleosides, and carbohydrates.
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