BROWSE

Related Scientist

CCHF's photo.

CCHF
분자활성 촉매반응 연구단
more info

ITEM VIEW & DOWNLOAD

Switching Chemoselectivity Based on the Ring Size: How to Make Ring-Fused Indoles Using Transition-Metal-Mediated Cross-Coupling

Cited 0 time in webofscience Cited 0 time in scopus
13 Viewed 0 Downloaded
Title
Switching Chemoselectivity Based on the Ring Size: How to Make Ring-Fused Indoles Using Transition-Metal-Mediated Cross-Coupling
Author(s)
Kim, Jang-Yeop; Woojong Lee; Kang, Hyung-Joon; Jeon, Tae-Hong; Mu-Hyun Baik; Cho, Cheon-Gyu
Publication Date
2021-10-15
Journal
ACS Catalysis, v.11, no.20, pp.12821 - 12832
Publisher
American Chemical Society
Abstract
© 2021 American Chemical SocietyPyrroloazocine indole alkaloids consisting of eight-membered azacycle fused to pyrrole and indole units exhibit intriguing pharmacological functions but still pose a synthetic challenge. Here, we report an alternative synthetic strategy for the pyrroloazocine indole core from two key steps: (i) regioselective Fischer indolization and (ii) transition-metal-mediated C-N cross-coupling reaction ofN-Boc aryl hydrazine with azacyclic vinyl triflate. In our investigation, Pd(0)- and Cu(I)-catalysts are found to display distinct and complementary selectivities for the ring size of cyclic vinyl triflates. For rings that are five- and six-membered, a Pd(0)-catalyst afforded the corresponding ene-hydrazines while completely ineffective for seven-membered or larger rings. A Cu(I)-catalyst exhibited the opposite selectivities. Computational studies reveal that their ring size dependency is due to the two bottlenecks of reductive elimination for Pd and oxidative addition for Cu along with bond strengths in products and reactants and degree of stage at transition states. These findings led us to establish a straightforward protocol for accessing a variety of ring-fused indoles highlighted with the formal synthesis of (−)-lundurine A.
URI
https://pr.ibs.re.kr/handle/8788114/10639
DOI
10.1021/acscatal.1c03797
ISSN
2155-5435
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
Files in This Item:
There are no files associated with this item.

qrcode

  • facebook

    twitter

  • Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.
해당 아이템을 이메일로 공유하기 원하시면 인증을 거치시기 바랍니다.

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

Browse