TY  - JOUR
A1  - Huang, Mingming
A1  - Hu, Jiefeng
A1  - Shi, Shasha
A1  - Friedrich, Alexandra
A1  - Krebs, Johannes
A1  - Westcott, Stephen A.
A1  - Radius, Udo
A1  - Marder, Todd B.
T1  - Selective, Transition Metal-free 1,2-Diboration of Alkyl Halides, Tosylates, and Alcohols
JF  - Chemistry-A European Journal
N2  - Defunctionalization of readily available feedstocks to provide alkenes for the synthesis of multifunctional molecules represents an extremely useful process in organic synthesis. Herein, we describe a transition metal-free, simple and efficient strategy to access alkyl 1,2-bis(boronate esters) via regio- and diastereoselective diboration of secondary and tertiary alkyl halides (Br, Cl, I), tosylates, and alcohols. Control experiments demonstrated that the key to this high reactivity and selectivity is the addition of a combination of potassium iodide and N,N-dimethylacetamide (DMA). The practicality and industrial potential of this transformation are demonstrated by its operational simplicity, wide functional group tolerance, and the late-stage modification of complex molecules. From a drug discovery perspective, this synthetic method offers control of the position of diversification and diastereoselectivity in complex ring scaffolds, which would be especially useful in a lead optimization program.
KW  - organic synthesis
KW  - boronate esters
KW  - alkyl halides
Y1  - 2022
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-318262
VL  - 28
IS  - 24
ER  -