Chemoselective Generation of the 1,3-Benzdiyne Synthon.
- 1Department of Chemistry for Life Sciences, Uppsala University, Box 576, 75123Uppsala, Sweden.
- 2Department of Chemistry - Ångström Laboratory, Uppsala University, Box 523, 75120Uppsala, Sweden.
- 3School of Chemistry, University of Bristol, Cantock's Close, Clifton, BristolBS8 1TS, United Kingdom.
Abstract
A versatile 1,3-benzdiyne precursor is reported that enables chemoselective, sequential generation of aryne triple bonds on the same aromatic ring under mild conditions. This is achieved from a single aromatic ring bearing an iodonium unit─enabling access to one aryne triple bond via deprotonation─and a "Kobayashi"-type ortho-silylaryl triflate unit, from which the second aryne triple bond can be released using fluoride. Each triple bond undergoes regioselective trapping. DFT studies reveal high-to-very high levels of ground state distortion in each aryne system. The approach leverages the unique reactivity of arynes to construct the framework of prized fluoride-activated precursors used in the next step. This strategy grants modular access to otherwise difficult-to-generate 1,2,3,4-substitution motifs.
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BibTeX
@article{barna2026chemoselective,
title = {{Chemoselective Generation of the 1,3-Benzdiyne Synthon.}},
author = {Fredrik Barnå and Manoj D Patil and Fredric J L Ingner and Andreas Orthaber and Paul J Gates and Lukasz T Pilarski},
journal = {The Journal of organic chemistry},
year = {2026},
month = sep,
doi = {10.1021/acs.joc.6c00616},
url = {https://europepmc.org/article/MED/42917090},
note = {CC BY},
}
RIS
TY - JOUR
TI - Chemoselective Generation of the 1,3-Benzdiyne Synthon.
AU - Fredrik Barnå
AU - Manoj D Patil
AU - Fredric J L Ingner
AU - Andreas Orthaber
AU - Paul J Gates
AU - Lukasz T Pilarski
PY - 2026
DA - 2026/09/01
JO - The Journal of organic chemistry
DO - 10.1021/acs.joc.6c00616
UR - https://europepmc.org/article/MED/42917090
AB - A versatile 1,3-benzdiyne precursor is reported that enables chemoselective, sequential generation of aryne triple bonds on the same aromatic ring under mild conditions. This is achieved from a single aromatic ring bearing an iodonium unit─enabling access to one aryne triple bond via deprotonation─and a "Kobayashi"-type ortho-silylaryl triflate unit, from which the second aryne triple bond can be released using fluoride. Each triple bond undergoes regioselective trapping. DFT studies reveal high-to-very high levels of ground state distortion in each aryne system. The approach leverages the unique reactivity of arynes to construct the framework of prized fluoride-activated precursors used in the next step. This strategy grants modular access to otherwise difficult-to-generate 1,2,3,4-substitution motifs.
SN - 0022-3263
SN - 1520-6904
ER -