Metal‐Free Decarboxylative A 3 ‐Coupling/Pictet–Spengler Cascade Accessing Polycyclic Scaffolds: Propiolic Acids Exceed Alkynes | Zendy

Hu Yingxin | Zendy; Shen Yangpeng | Zendy; Huang Liliang | Zendy; Van der Eycken Erik V. | Zendy; Feng Huangdi | Zendy

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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.

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