1222085-64-4Relevant academic research and scientific papers
Palladium-catalyzed chemoselective allylic substitution, suzuki-miyaura cross-coupling, and allene formation of bifunctional 2-B(pin)-substituted allylic acetate derivatives
Kim, Byeong-Seon,Hussain, Mahmud M.,Hussain, Nusrah,Walsh, Patrick J.
, p. 11726 - 11739 (2014)
A formidable challenge at the forefront of organic synthesis is the control of chemoselectivity to enable the selective formation of diverse structural motifs from a readily available substrate class. Presented herein is a detailed study of chemoselectivity with palladium-based phosphane catalysts and readily available 2-B(pin)-substituted allylic acetates, benzoates, and carbonates. Depending on the choice of reagents, catalysts, and reaction conditions, 2-B(pin)-substituted allylic acetates and derivatives can be steered into one of three reaction manifolds: allylic substitution, Suzuki-Miyaura cross-coupling, or elimination to form allenes, all with excellent chemoselectivity. Studies on the chemoselectivity of Pd catalysts in their reactivity with boron-bearing allylic acetate derivatives led to the development of diverse and practical reactions with potential utility in synthetic organic chemistry.
Allylie substitution versus Suzuki cross-coupling: Capitalizing on chemoselectivity with bifunctional substrates
Hussain, Mahmud M.,Walsh, Patrick J.
supporting information; experimental part, p. 1834 - 1837 (2010/06/21)
One catalyst, two reactions-a tale of chemoselectivity: Given the choice between an allylic acetate and a vinylboronate ester, palladium preferentially reacts with the allylic acetate to give the allylic substitution product. In the presence of an aryl bromide and base, Suzuki cross-coupling subsequently ensues to afford allylic amines (see scheme; pin = pinacol, THF = tetrahydrofuran). Chemical equation representation
