TY - JOUR
T1 - Recent topics of iridium-catalyzed hydrosilylation of tertiary amides to silylhemiaminals
AU - Tahara, Atsushi
AU - Nagashima, Hideo
N1 - Funding Information:
This work was supported by Integrated Research Consortium on Chemical Sciences (IRCCS), the Cooperative Research Program of “Network Joint Research Center for Materials and Devices”, and JSPS KAKENHI Grant Numbers JP18H01980 , JP18K19082 , JP17K17944 and JP19K05504 .
Funding Information:
This work was supported by Integrated Research Consortium on Chemical Sciences (IRCCS), the Cooperative Research Program of ?Network Joint Research Center for Materials and Devices?, and JSPS KAKENHI Grant Numbers JP18H01980, JP18K19082, JP17K17944 and JP19K05504.
Publisher Copyright:
© 2019
PY - 2020/1/23
Y1 - 2020/1/23
N2 - Iridium-catalyzed hydrosilylation of amides with 1,1,3,3-tetramethyldisiloxane (TMDS) allows access to silylhemiaminals, which are often spontaneously converted to aldenamines. Iridium(I) phosphine species generated from IrCl(CO)(PPh3)2, IrCl(PPh3)3, or a mixture of [IrCl(COD)]2 and phosphorous ligands showed high catalytic activity for this reaction protocol, which demonstrated remarkable compatibility toward other reducible functional groups such as ketone and ester groups. This reaction enables the synthesis of π-conjugate enamines having hole-transport properties by appropriate selection of the iridium catalyst. Easy access to silyl hemiaminals and enamined stimulated other research groups to discover new reductive C–C bond-forming reactions to transform amides to amine derivatives, which can be applied to the synthesis of complex alkaloid molecules.
AB - Iridium-catalyzed hydrosilylation of amides with 1,1,3,3-tetramethyldisiloxane (TMDS) allows access to silylhemiaminals, which are often spontaneously converted to aldenamines. Iridium(I) phosphine species generated from IrCl(CO)(PPh3)2, IrCl(PPh3)3, or a mixture of [IrCl(COD)]2 and phosphorous ligands showed high catalytic activity for this reaction protocol, which demonstrated remarkable compatibility toward other reducible functional groups such as ketone and ester groups. This reaction enables the synthesis of π-conjugate enamines having hole-transport properties by appropriate selection of the iridium catalyst. Easy access to silyl hemiaminals and enamined stimulated other research groups to discover new reductive C–C bond-forming reactions to transform amides to amine derivatives, which can be applied to the synthesis of complex alkaloid molecules.
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U2 - 10.1016/j.tetlet.2019.151423
DO - 10.1016/j.tetlet.2019.151423
M3 - Review article
AN - SCOPUS:85076750393
SN - 0040-4039
VL - 61
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 4
M1 - 151423
ER -