Lewis Acid Catalyzed Regioselective Hydroheteroarylation of Pentafulvenes

被引：10

作者：

Chand, S. Sarath ^{[1
,2
]}

Gopalan, Greeshma ^{[1
,2
]}

Santhini, P. V. ^{[1
,2
]}

Preethanuj, P. ^{[2
]}

John, Jubi ^{[2
]}

Harakat, Dominique ^{[3
]}

Jaroschik, Florian ^{[3
]}

Radhakrishnan, K. V. ^{[1
,2
]}

机构：

[1] Acad Sci & Innovat Res AcSIR, New Delhi 110001, India

[2] Natl Inst Interdisciplinary Sci & Technol CSIR, Organ Chem Sect, Trivandrum 695019, Kerala, India

[3] Univ Reims, Inst Chim Mol Reims CNRS UMR 7312, F-51687 Reims 2, France

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 05期

关键词：

H BOND ACTIVATION; INTERMOLECULAR HYDROARYLATION; CATIONIC POLYFULVENES; 6+3 CYCLOADDITION; INDOLE SYNTHESIS; FACILE SYNTHESIS; AROMATIC IMINES; METAL-COMPLEXES; DOMINO REACTION; FULVENES;

D O I：

10.1021/acs.orglett.6b00047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diverse approach toward the catalytic regioselective nucleophilic addition of nitrogen heterocycles to Lewis acid activated pentafulvenes has been established. The developed protocol introduces pentafulvenes as nonsymmetrical alkenes for the hydroheteroarylation reaction, providing alkylidenecyclopentenylation at the C-3 position of indoles and the C-2 position of pyrrole.

引用

页码：964 / 967

页数：4

共 50 条

[1] Pd(ii)/Lewis acid catalyzed regioselective olefination of indole with dioxygen
Tan, Chen
Jiang, Hongwu
Zeng, Miao
Li, Kaiwen
Chen, Zhuqi
Yin, Guochuan
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (07) : 1425 - 1435
[2] Lewis Acid Catalyzed α-Functionalization of Ketals for the Regioselective Synthesis of α-Carbamoyl Ketals
Magnus, Philip
Brozell, Alec J.
ORGANIC LETTERS, 2012, 14 (15) : 3952 - 3954
[3] Lewis Acid Catalyzed Regioselective Substitution of 2-Indolylmethanols with Pyrroles
Gao, Jun-Nan
Tan, Wen-Xin
Yang, Shuang
Wang, Ning-Yi
Han, Jiebin
Wang, Da-Hua
Zhang, Yu-Chen
Shi, Feng
SYNTHESIS-STUTTGART, 2025, 57 (06): : 1189 - 1198
[4] Lewis acid catalyzed regioselective ring opening of azetidines with alcohols and thiols
Dwivedi, Sandeep K.
Gandhi, Shikha
Rastogi, Narnrata
Singh, Vinod K.
TETRAHEDRON LETTERS, 2007, 48 (31) : 5375 - 5377
[5] Regioselective synthesis of pentacyclic heterocycles by the thermal and Lewis acid catalyzed Claisen rearrangement
Majumdar, K. C.
Pal, A. K.
JOURNAL OF SULFUR CHEMISTRY, 2009, 30 (05) : 481 - 489
[6] Boron Lewis Acid-Catalyzed Regioselective Hydrothiolation of Conjugated Dienes with Thiols
Kumar, Gautam
Qu, Zheng-Wang
Ghosh, Soumen
Grimme, Stefan
Chatterjee, Indranil
ACS CATALYSIS, 2019, 9 (12) : 11627 - 11633
[7] Lewis Acid-catalyzed Regioselective Addition of Allenoates to Indoles for Synthesis of Bisindolylesters
Xie, Fuyu
He, Jianghua
Zhang, Yuetao
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2025, 41 (01) : 48 - 58
[8] Synthesis of β-lactones by the regioselective, cobalt and Lewis acid catalyzed carbonylation of simple and functionalized epoxides
Lee, JT
Thomas, PJ
Alper, H
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16): : 5424 - 5426
[9] Lewis-Acid-Catalyzed Regioselective Construction of Diversely Functionalized Polycyclic Fused Furans
Jamshaid, Sana
Lee, Yong Rok
ORGANIC LETTERS, 2022, 24 (06) : 1351 - 1356
[10] Lewis acid catalyzed Claisen rearrangement: Regioselective synthesis of oxygen, nitrogen, and sulfur heterocycles
Majumdar, K. C.
Pal, A. K.
CANADIAN JOURNAL OF CHEMISTRY, 2008, 86 (01) : 72 - 78

← 1 2 3 4 5 →