Photoinduced Vitamin B12-Catalysis for Deprotection of (Allyloxy)arenes

Maciej Giedyk; Joanna Turkowska; Sandra Lepak; Marcin Marculewicz; Keith Ó Proinsias; Dorota Gryko

doi:10.1021/acs.orglett.7b01012

Photoinduced Vitamin B₁₂-Catalysis for Deprotection of (Allyloxy)arenes

Org Lett. 2017 May 19;19(10):2670-2673. doi: 10.1021/acs.orglett.7b01012. Epub 2017 Apr 28.

Authors

Maciej Giedyk¹, Joanna Turkowska¹, Sandra Lepak¹, Marcin Marculewicz¹, Keith Ó Proinsias¹, Dorota Gryko¹

Affiliation

¹ Institute of Organic Chemistry Polish Academy of Science , Kasprzaka 44/52, 01-224 Warsaw, Poland.

PMID: 28453294
DOI: 10.1021/acs.orglett.7b01012

Abstract

Vitamin B₁₂ is a natural cobalt complex that, while reduced to the "supernucleophilic" Co(I) form, can easily react with electrophiles via an S_N2 mechanism. It is also shown to react via an S_N2' mechanism with allylic compounds allowing for photochemical deprotection of (allyloxy)arenes. A sustainable alternative to commonly used noble metal-catalyzed deprotection reactions is presented.

Publication types

Research Support, Non-U.S. Gov't