Insights into the gold(i)-catalyzed intermolecular annulations of alkynes with N-allenamides: a mechanistic DFT study

Author:

Sun Qing1ORCID,Deng Tian-Yu2,Chen Jia-Jie1,Liu Jia-Yi1,Lu Xin3ORCID,Zhang Zhi-Xia1,Li Jin-Heng14ORCID

Affiliation:

1. Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China

2. Department of Chemical Engineering, Tsinghua University, Beijing 100084, China

3. State Key Laboratory of Physical Chemistry of Solid Surface & Fujian Provincial Key Laboratory for Theoretical and Computational Chemistry, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China

4. School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 475004, China

Abstract

The Au(i)-catalyzed intermolecular annulation of 2-(1-alkynyl)-2-alken-1-one 1a with N-allenamide 2a is driven by the higher reactivity of the gold all-carbon 1,3-dipole species A than the gold allylic carbocation B, rather than the easier access to A.

Funder

Jiangxi Provincial Department of Science and Technology

Data Center of Management Science, National Natural Science Foundation of China - Peking University

Publisher

Royal Society of Chemistry (RSC)

Subject

Inorganic Chemistry

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