Zinc-Catalyzed Alkyne Oxidation/C-H Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines

Long Li; Bo Zhou; Yong-Heng Wang; Chao Shu; Yi-Fei Pan; Xin Lu; Long-Wu Ye

doi:10.1002/anie.201502553

Zinc-Catalyzed Alkyne Oxidation/C-H Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines

Angew Chem Int Ed Engl. 2015 Jul 6;54(28):8245-9. doi: 10.1002/anie.201502553. Epub 2015 May 27.

Authors

Long Li¹, Bo Zhou¹, Yong-Heng Wang², Chao Shu¹, Yi-Fei Pan¹, Xin Lu³, Long-Wu Ye⁴

Affiliations

¹ State Key Laboratory for Physical Chemistry of Solid Surfaces & The Key Laboratory for Chemical Biology of Fujian Province, Department of Chemistry, Xiamen University, Xiamen 361005 (China).
² State Key Laboratory of Physical Chemistry of Solid Surfaces & Center for Theoretical Chemistry, Department of Chemistry, Xiamen University, Xiamen 361005 (China).
³ State Key Laboratory of Physical Chemistry of Solid Surfaces & Center for Theoretical Chemistry, Department of Chemistry, Xiamen University, Xiamen 361005 (China). xinlu@xmu.edu.cn.
⁴ State Key Laboratory for Physical Chemistry of Solid Surfaces & The Key Laboratory for Chemical Biology of Fujian Province, Department of Chemistry, Xiamen University, Xiamen 361005 (China). longwuye@xmu.edu.cn.

PMID: 26013998
DOI: 10.1002/anie.201502553

Abstract

An efficient zinc(II)-catalyzed alkyne oxidation/C-H functionalization sequence was developed, thus leading to highly site-selective synthesis of a variety of isoquinolones and β-carbolines. Importantly, in contrast to the well-established gold-catalyzed intermolecular alkyne oxidation, over-oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel-Crafts-type pathway. Mechanistic studies and theoretical calculations are described.

Keywords: heterocycles; homogeneous catalysis; nitrogen oxides; synthetic methods; zinc.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acids, Heterocyclic / chemistry*
Carbolines / chemistry*
Catalysis
Nitrogen Oxides / chemistry*
Oxidation-Reduction
Zinc / chemistry*

Substances

Acids, Heterocyclic
Carbolines
Nitrogen Oxides
Zinc