期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 31, 页码 12789-12794出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202004950
关键词
alkyne; arylation; homogeneous catalysis; manganese; selectivity
资金
- National Natural Science Foundation of China [21971108, 21702098, 21703118]
- Fundamental Research Funds for the Central Universities [020514380214]
- Natural Science Foundation of Jiangsu Province [BK20190006, BK20190285]
- Innovation & Entrepreneurship Talents Plan of Jiangsu Province, Jiangsu Six Peak Talent Project, Shandong Provincial Natural Science Foundation [ZR2017MB038]
- 1000-Youth Talent Plan
- Nanjing University
- High Performance Computing Center of Qufu Normal University
We have developed a general and site-predictable manganese-catalyzed hydroarylation of internal alkynes in the presence of water, under an air atmosphere without the involvement of ligand. The unique catalytic feature of this reaction is highlighted by comparison with other widely used transition metal catalysts including palladium, rhodium, nickel, or copper. The simple operation, high efficiency and excellent functional group compatibility make this protocol practical for more than 90 structurally diverse internal alkynes, overcoming the influence of both electronic and steric effect of alkynes. Its exclusive regio- and chemoselectivity originates from the unique reactivity of the manganese-based catalyst towards an inherent double controlled strategy of sterically hindered propargyl alcohols without the installing of external directing groups. Its synthetic robustness and practicality have been illustrated by the concise synthesis of bervastatin, a hypolipidemic drug, and late-stage modification of complex alkynes with precise regioselectivity.
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