TY - JOUR
T1 - Synthesis of Two Types of Nitriles Both Bearing Quaternary Carbon Centers in One-Pot Manner
AU - Ren, Xinyi
AU - Wang, Guangzhu
AU - Ji, Xiaolei
AU - Dong, Kaiwu
N1 - Publisher Copyright:
© 2022 Chinese Chemical Society & SIOC, CAS.
PY - 2022/2
Y1 - 2022/2
N2 - α-Bromocarboxamides and electrophilic cyanide reagent were transformed into the corresponding α-cyanocarboxamides and ketene imine zinc intermediate in the presence of Zn reductant. Trapping of such Zn species with additional electrophiles resulted another type of nitriles, which realized the synthesis of two types of nitriles both bearing quaternary carbon centers in one-pot manner. This approach could be used to construct C-C, C-S, or C-F bond. Formal synthesis of several key pharmaceutical intermediates including loperamide, proadifen, verapamil, and gallopamil as well as α-fluoroibuprofen and α-fluoroflurbiprofen demonstrated the potential application of this methodology.
AB - α-Bromocarboxamides and electrophilic cyanide reagent were transformed into the corresponding α-cyanocarboxamides and ketene imine zinc intermediate in the presence of Zn reductant. Trapping of such Zn species with additional electrophiles resulted another type of nitriles, which realized the synthesis of two types of nitriles both bearing quaternary carbon centers in one-pot manner. This approach could be used to construct C-C, C-S, or C-F bond. Formal synthesis of several key pharmaceutical intermediates including loperamide, proadifen, verapamil, and gallopamil as well as α-fluoroibuprofen and α-fluoroflurbiprofen demonstrated the potential application of this methodology.
KW - Electrophilic cyanide reagent
KW - Nitrile
KW - Pharmaceutical intermediate
KW - Quaternary carbon center
UR - https://www.scopus.com/pages/publications/85126305354
U2 - 10.6023/cjoc202107017
DO - 10.6023/cjoc202107017
M3 - 文章
AN - SCOPUS:85126305354
SN - 0253-2786
VL - 42
SP - 526
EP - 533
JO - Chinese Journal of Organic Chemistry
JF - Chinese Journal of Organic Chemistry
IS - 2
ER -