TY - JOUR
T1 - A highly efficient Hg(OTf)2-mediated Sakurai-Hosomi allylation of
T2 - N-tert -butyloxycarbonylamino sulfones, aldehydes, fluoroalkyl ketones and α,β-unsaturated enones using allyltrimethylsilane
AU - Gong, Yi
AU - Cao, Zhong Yan
AU - Shi, Ying Bo
AU - Zhou, Feng
AU - Zhou, Ying
AU - Zhou, Jian
N1 - Publisher Copyright:
© 2019 the Partner Organisations.
PY - 2019/12/21
Y1 - 2019/12/21
N2 - It is reported that cheap and easily available Hg(OTf)2 can efficiently mediate the Sakurai-Hosomi reaction of N-tert-butyloxycarbonyl (Boc) amino sulfones, aldehydes, and α-fluoroalkyl ketones using allyltrimethylsilane, with the catalyst loading down to 0.5-5.0 mol%, enabling the facile access to synthetically valuable homoallylic alcohols or amines, respectively. A chemoselective 1,4-allylation of α,β-unsaturated enones is also achieved under the catalysis of 5.0 mol% Hg(OTf)2. In most cases, Hg(OTf)2 exhibited intriguing properties superior to those of commonly used metal Lewis acids for such reactions, suggesting that mercury catalysis is worthwhile to explore.
AB - It is reported that cheap and easily available Hg(OTf)2 can efficiently mediate the Sakurai-Hosomi reaction of N-tert-butyloxycarbonyl (Boc) amino sulfones, aldehydes, and α-fluoroalkyl ketones using allyltrimethylsilane, with the catalyst loading down to 0.5-5.0 mol%, enabling the facile access to synthetically valuable homoallylic alcohols or amines, respectively. A chemoselective 1,4-allylation of α,β-unsaturated enones is also achieved under the catalysis of 5.0 mol% Hg(OTf)2. In most cases, Hg(OTf)2 exhibited intriguing properties superior to those of commonly used metal Lewis acids for such reactions, suggesting that mercury catalysis is worthwhile to explore.
UR - https://www.scopus.com/pages/publications/85076102295
U2 - 10.1039/c9qo01049a
DO - 10.1039/c9qo01049a
M3 - 文章
AN - SCOPUS:85076102295
SN - 2052-4110
VL - 6
SP - 3989
EP - 3995
JO - Organic Chemistry Frontiers
JF - Organic Chemistry Frontiers
IS - 24
ER -