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Title: An enantioconvergent halogenophilic nucleophilic substitution (SN2X) reaction
Authors: Zhang, Xin
Ren, Jingyun
Tan, Siu Min
Tan, Davin
Lee, Richmond
Tan, Choon-Hong
Keywords: Science::Chemistry
Issue Date: 2019
Source: Zhang, X., Ren, J., Tan, S. M., Tan, D., Lee, R. & Tan, C. (2019). An enantioconvergent halogenophilic nucleophilic substitution (SN2X) reaction. Science, 363(6425), 400-404.
Project: M4011663
Journal: Science
Abstract: Bimolecular nucleophilic substitution (SN2) plays a central role in organic chemistry. In the conventionally accepted mechanism, the nucleophile displaces a carbon-bound leaving group X, often a halogen, by attacking the carbon face opposite the C–X bond. A less common variant, the halogenophilic SN2X reaction, involves initial nucleophilic attack of the X group from the front and as such is less sensitive to backside steric hindrance. Herein, we report an enantioconvergent substitution reaction of activated tertiary bromides by thiocarboxylates or azides that, on the basis of experimental and computational mechanistic studies, appears to proceed via the unusual SN2X pathway. The proposed electrophilic intermediates, benzoylsulfenyl bromide and bromine azide, were independently synthesized and shown to be effective.
ISSN: 0036-8075
DOI: 10.1126/science.aau7797
Rights: © 2019 The Author(s), some rights reserved; exclusive licensee American Association for the Advancement of Science.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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