Journal
ORGANIC LETTERS
Volume 21, Issue 7, Pages 2251-2255Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00531
Keywords
-
Categories
Funding
- Spanish Ministerio de Economia y competitividad (MINECO) [FEDER-CTQ2016-80328-P]
- Generalitat de Catalunya [2017SGR629]
Ask authors/readers for more resources
This work explains the reactivity of diboron reagents with 1,3-dienes in a transition-metal-free context. The sole addition of Na2CO3 (30 mol %) to bis(pinacolato)diboron in MeOH allows the 1,4-hydroboration of cyclic and noncyclic 1,3-dienes. The electronic influence on the substrate guarantees the conjugated 1,4-hydroboration versus 1,2-diboration. DFT calculations show that the distribution of charge in the allylic anion intermediate governs the selectivity toward 1,4-hydroboration, while the favored trans configuration in diene reagents determines the preference for the E allyl boronate products.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available