Journal
NATURE COMMUNICATIONS
Volume 10, Issue -, Pages -Publisher
NATURE PORTFOLIO
DOI: 10.1038/s41467-019-12102-y
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Funding
- National Natural Science Foundation of China [21773222, U1732272, 21573204, 51772285]
- National Key RAMP
- D Program of China [2017YFA0403402, 2016YFA0200602, 2018YFA0208603]
- DNL Cooperation Fund, CAS [DNL180201]
- CAS Interdisciplinary Innovation Team, Anhui Initiative in Quantum Information Technology [AHY090400]
- Fundamental Research Funds for the Central Universities
- National Program for Support of Top-Notch Young Professional
- Supercomputer Center of USTCSCC
- CAS President's International Fellowship Initiative
- Supercomputer Center of SCCAS
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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 sub-stituents 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.
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