[Thu. 18 May. 2017] Student Host Colloquium : 1,1-Bisborylalkane: New Class of Organoboron Compound for the Chemo, Regio and Stereoselective Organic Transformations

“1,1-Bisborylalkane: New Class of Organoboron Compound

for the Chemo, Regio and Stereoselective Organic Transformations”

1,1-Organodimetallic reagents are valuable starting materials for the construction of multifunctionalized molecules. Among them, 1,1-diborylalkanes, which contain two boryl groups at the same carbon center, are particularly attractive due to their ease of handling, non-toxicity, stability, and propensity to undergo a variety of organic transformations. In this context, our lab is highly interested in the development of regio, chemo and stereoselective organic reactions using 1,1-diborylalkanes as new types of organodimetallic reagents.

In this seminar, the details about our recent findings using 1,1-diborylalkanes in a range of organic transformations will be presented including 1) copper-catalyzed SN2’-selective allylic substitution reactions of allylic chlorides with1,1-diborylalkanes 2)the chemo- and diastereoselective alkylation ofN-tert-butanesulfinyl aldimines. 3) an unprecedented transition-metal-free deborylative alkylation of pyridine N-oxides using 1,1-diboryl-alkanes as alkyl sources and 4) an unusual chemoselective coupling of 1,1-diborylalkanes for the transition-metal-free borylation of aryl and vinyl halides.

References

Kim, J.; Park, S.; Park, J.; Cho, S. H.* Angew. Chem., Int. Ed. 2016, 55, 1498.

Park, J.; Lee, Y. Kim, J. Cho, S. H.* Org. Lett. 2016, 18, 1210.

Cho, W.; Kim, J.; Choi, S. Cho, S. H.* Angew. Chem., Int. Ed. 2016, 55, 9690

Kim, J.; Cho, S. H.* Synlett, 2016, 27, 2525. (Invited contribution of Synpact article)

Lee, Y.; Baek, S.; Park, J.; Kim, S. T.; Tussupbayev, S.; Kim, J.; Baik, M. Cho, S. H J. Am. Chem. Soc.2017, 139, 976.

Prof. Seung Hwan Cho

Department of Chemistry, POSTECH, Pohang, Republic of Korea