Abstract
Substituted 1,3-dienes are valuable synthetic intermediates used in myriad catalytic transformations, yet modern catalytic methods for their preparation in a highly modular fashion using simple precursors are relatively few. We report here an aerobic boron Heck reaction with cyclobutene that forms exclusively linear 1-aryl-1,3-dienes using (hetero)arylboronic acids, or 1,3,5-trienes using alkenylboronic acids, rather than typical Heck products (i.e., substituted cyclobutenes). Experimental and computational mechanistic data support a pericyclic mechanism for C-C bond cleavage that enables the cycloalkene to circumvent established limitations associated with diene reagents in Heck-type reactions.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 13634-13639 |
| Number of pages | 6 |
| Journal | Journal of the American Chemical Society |
| Volume | 140 |
| Issue number | 42 |
| DOIs | |
| State | Published - Oct 24 2018 |
All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
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McAlpine, N. J., Wang, L., & Carrow, B. P. (2018). A Diverted Aerobic Heck Reaction Enables Selective 1,3-Diene and 1,3,5-Triene Synthesis through C-C Bond Scission. Journal of the American Chemical Society, 140(42), 13634-13639. https://doi.org/10.1021/jacs.8b10007