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Metal‐Free Decarboxylative A 3 ‐Coupling/Pictet–Spengler Cascade Accessing Polycyclic Scaffolds: Propiolic Acids Exceed Alkynes
Author(s) -
Hu Yingxin,
Shen Yangpeng,
Huang Liliang,
Van der Eycken Erik V.,
Feng Huangdi
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000007
Subject(s) - chemistry , cascade , pictet–spengler reaction , alkyne , propargyl , formaldehyde , decarboxylation , electrocyclic reaction , organic chemistry , metal , combinatorial chemistry , catalysis , bicyclic molecule , chromatography
Herein, we describe the development of a metal‐free decarboxylative A 3 ‐coupling and Pictet–Spengler cascade process to directly generate functionalized tetrahydroisoquinolines from a 2‐phenylethanamine, formaldehyde, and a propiolic acid. The key feature of this efficient reactivity is the utilization of a propiolic acid as the alkyne source, with TFA as promoter. This transformation was also demonstrated to be amenable to the construction of N ‐propargyl thienotetrahydropyridine and benzodiazepine skeletons under mild conditions.