Reaction selectivity of homochiral versus heterochiral intermolecular reactions of prochiral terminal alkynes on surfaces

Tao Wang, Haifeng Lv, Jianmin Huang, Huan Shan, Lin Feng, Yahui Mao, Jinyi Wang, Wenzhao Zhang, Dong Han, Qian Xu, Pingwu Du, Aidi Zhao (), Xiaojun Wu (), Steven L. Tait and Junfa Zhu ()
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Tao Wang: University of Science and Technology of China
Haifeng Lv: University of Science and Technology of China
Jianmin Huang: University of Science and Technology of China
Huan Shan: University of Science and Technology of China
Lin Feng: University of Science and Technology of China
Yahui Mao: University of Science and Technology of China
Jinyi Wang: University of Science and Technology of China
Wenzhao Zhang: University of Science and Technology of China
Dong Han: University of Science and Technology of China
Qian Xu: University of Science and Technology of China
Pingwu Du: University of Science and Technology of China
Aidi Zhao: University of Science and Technology of China
Xiaojun Wu: University of Science and Technology of China
Steven L. Tait: Indiana University
Junfa Zhu: University of Science and Technology of China

Nature Communications, 2019, vol. 10, issue 1, 1-9

Abstract: Abstract Controlling selectivity between homochiral and heterochiral reaction pathways on surfaces remains a great challenge. Here, competing reactions of a prochiral alkyne on Ag(111): two-dimensional (2D) homochiral Glaser coupling and heterochiral cross-coupling with a Bergman cyclization step have been examined. We demonstrate control strategies in steering the reactions between the homochiral and heterochiral pathways by tuning the precursor substituents and the kinetic parameters, as confirmed by high-resolution scanning probe microscopy (SPM). Control experiments and density functional theory (DFT) calculations reveal that the template effect of organometallic chains obtained under specific kinetic conditions enhances Glaser coupling between homochiral molecules. In contrast, for the reaction of free monomers, the kinetically favorable reaction pathway is the cross-coupling between two heterochiral molecules (one of them involving cyclization). This work demonstrates the application of kinetic control to steer chiral organic coupling pathways at surfaces.

Date: 2019
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DOI: 10.1038/s41467-019-12102-y

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