TY - JOUR
T1 - Turning Waste into Valuable Catalysts
T2 - Application of Surface-Modified Sewage Sludge in N-H Insertion Reaction
AU - Yi, Xiangyan
AU - Yu, Yang
AU - Huang, Fei
AU - Ding, Tianxing
AU - Zhang, Zhipeng
AU - Feng, Jiajun
AU - Baell, Jonathan Bayldon
AU - Huang, He
PY - 2020/3/18
Y1 - 2020/3/18
N2 - Given the unique properties of sewage sludge-derived carbonaceous materials (SC) and the correlation of SC with recycling sewage sludge in an efficiently safe way, there is significant attraction from researchers to develop innovative methodologies that enable a more extensive application of SC. Applying SC in forming rather than cleaving chemical bonds is highly desirable to maximize the value of sewage sludge. Here, we report the surface-modified SC-catalyzed N-H insertion reaction of a wide range of α-aryl diazoesters with amines, which was first accomplished with moderate to good yield (86%). The catalytic performance of this catalyst is shown by a 10 gram-scale reaction and the synthesis of a drug molecule, (±)-clopidogrel. A mechanistic study suggests that the C-N bond formation involves ammonium ylide intermediates and hydrogen bonding. This discovery leads to the realization of a feasible strategy for sewage sludge recycling and a new avenue to catalyst research.
AB - Given the unique properties of sewage sludge-derived carbonaceous materials (SC) and the correlation of SC with recycling sewage sludge in an efficiently safe way, there is significant attraction from researchers to develop innovative methodologies that enable a more extensive application of SC. Applying SC in forming rather than cleaving chemical bonds is highly desirable to maximize the value of sewage sludge. Here, we report the surface-modified SC-catalyzed N-H insertion reaction of a wide range of α-aryl diazoesters with amines, which was first accomplished with moderate to good yield (86%). The catalytic performance of this catalyst is shown by a 10 gram-scale reaction and the synthesis of a drug molecule, (±)-clopidogrel. A mechanistic study suggests that the C-N bond formation involves ammonium ylide intermediates and hydrogen bonding. This discovery leads to the realization of a feasible strategy for sewage sludge recycling and a new avenue to catalyst research.
UR - http://www.scopus.com/inward/record.url?scp=85082744672&partnerID=8YFLogxK
U2 - 10.1021/acs.iecr.9b05709
DO - 10.1021/acs.iecr.9b05709
M3 - Article
AN - SCOPUS:85082744672
SN - 0888-5885
VL - 59
SP - 4854
EP - 4863
JO - Industrial & Engineering Chemistry Research
JF - Industrial & Engineering Chemistry Research
IS - 11
ER -