Aluminum-Catalyzed Cross Selective C3-N1′ Coupling Reactions of N-Methoxyindoles with Indoles

被引：2

作者：

Tokushige, Keisuke ^{[1
]}

Yamashiro, Toshiki ^{[1
]}

Hirao, Seiya ^{[1
]}

Abe, Takumi ^{[1
]}

机构：

[1] Okayama Univ, Grad Sch Med Dent & Pharmaceut Sci, Okayama 7008530, Japan

来源：

CHEMISTRY-SWITZERLAND | 2023年 / 5卷 / 01期

关键词：

1 ' H-1,3 '-biindole; N-electrophilic; N-methoxyindoles; bisindoles; aluminum; cross-coupling; NUCLEOPHILIC-SUBSTITUTION REACTION; ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; FUNCTIONALIZATION; 1-HYDROXYINDOLES; CHEMISTRY; NITROGEN; NUCLEUS; ROUTE; METAL;

D O I：

10.3390/chemistry5010033

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

C3-N1 ' bond formation of bisindoles has been a great challenge due to the intrinsic reactivity of indoles as both C3 and N1-nucleophilic character. Herein, we demonstrate an C3-N1 ' cross-coupling reaction of indoles using N-methoxyindoles as N-electrophilic indole reagents in the presence of Lewis acid. The bisindoles generated in this transformation are latent C3-nucleophile, allowing them to be used as strategic intermediates in sequential C3-N1 '-C3 '-N1 '' triindole formations. The potential synthetic usefulness of this sequential transformation was highlighted upon application to the construction of C3-N1 looped polyindoles.

引用

页码：452 / 462

页数：11

共 50 条

[1] Aluminum-Catalyzed Cross-Coupling of Silylalkynes with Aliphatic C-F Bonds
Jaiswal, Amit K.
Goh, Kelvin K. K.
Sung, Simon
Young, Rowan D.
ORGANIC LETTERS, 2017, 19 (07) : 1934 - 1937
[2] Synthetic strategies for the construction of C3-N1′ bisindoles
Abe, Takumi
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (09) : 1756 - 1764
[3] Advances on N-Arylation of Indoles by Cross-Coupling Reactions
Xu, Hui
MINI-REVIEWS IN ORGANIC CHEMISTRY, 2009, 6 (04) : 367 - 377
[4] Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions
Ruiz-Castillo, Paula
Buchwald, Stephen L.
CHEMICAL REVIEWS, 2016, 116 (19) : 12564 - 12649
[5] Palladium-Catalyzed C,N-Cross Coupling Reactions of 3-Halo-2-aminopyridines
Perez, Felix
Minatti, Ana
ORGANIC LETTERS, 2011, 13 (08) : 1984 - 1987
[6] Development of catalysts for Pd-catalyzed C-N cross-coupling reactions
Fors, Brett P.
Buchwald, Stephen L.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[7] Palladium–catalyzed C–C– and C–N–coupling reactions of aryl chlorides
Thomas H. Riermeier
Alexander Zapf
Matthias Beller
Topics in Catalysis, 1997, 4 : 301 - 309
[8] Highly selective room-temperature copper-catalyzed C-N coupling reactions
Shafir, Alexandr
Buchwald, Stephen L.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (27) : 8742 - 8743
[9] N-Heterocyclic Carbene-Catalyzed Cross-Coupling of Aldehydes with Arylsulfonyl Indoles
Li, Yi
Shi, Fu-Qiang
He, Qing-Li
You, Shu-Li
ORGANIC LETTERS, 2009, 11 (15) : 3182 - 3185
[10] Transition-metal-catalyzed C-N cross-coupling reactions of N-unsubstituted sulfoximines: a review
Hosseinian, Akram
Fekri, Leila Zare
Monfared, Aazam
Vessally, Esmail
Nikpassand, Mohammad
JOURNAL OF SULFUR CHEMISTRY, 2018, 39 (06) : 674 - 698

← 1 2 3 4 5 →