Rhodium-Catalyzed Annulation of 4-Arylbut-3-yn-1-amines with Internal Alkynes through C-H Functionalization

被引：23

作者：

Li, Yang ^{[1
]}

Pi, Rui ^{[1
]}

Ouyang, Xuan-Hui ^{[1
]}

Song, Ren-Jie ^{[1
]}

Li, Jin-Heng ^{[1
,2
]}

机构：

[1] Nanchang Hangkong Univ, Key Lab Jiangxi Prov Persistent Pollutants Contro, Nanchang 330063, Jiangxi, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 02期

基金：

中国国家自然科学基金;

关键词：

INTRAMOLECULAR CYCLIZATION; C(SP(3))-H ACTIVATION; BOND FORMATION; CYCLOADDITION; CONSTRUCTION; ALKYNYLATION; TRANSFORMATIONS; ACRYLAMIDES; ANTIFUNGAL; AMIDATION;

D O I：

10.1021/acs.orglett.8b03561

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, one-step rhodium(III)-catalyzed annulation of 4-arylbut-3-yn-1-amines with internal alkynes through C-H functionalization is reported. This reaction allows the formation of three new chemical bonds, including two C-C bonds and one C-N band, thus selectively assembling various spiro[indene-1,2'-pyrrolidine]s with excellent functional group compatibility, high atom-economy, and step-efficiency.

引用

页码：397 / 400

页数：4

共 79 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations
Ackermann, Lutz
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) : 281 - 295
[2] Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition of Unsymmetrical α,ω-Diynes with Acenaphthylene
Aida, Yukimasa
Shibata, Yu
Tanaka, Ken
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (05) : 2617 - 2626
[3] AlvarezBuilla J, 2011, MODERN HETEROCYCLIC CHEMISTRY, VOL 4, P1, DOI 10.1002/9783527637737
[4] Rhodium(III)-Catalyzed Allylic C(sp3)-H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles
Archambeau, Alexis
Rovis, Tomislav
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (45) : 13337 - 13340
[5] Azizian J., 2004, SYNTHESIS-STUTTGART, V2004, P2263
[6] Heteropolyacid-silica mediated [3+2] cycloaddition of azomethine ylides - a facile multicomponent one-pot synthesis of novel dispiroheterocycles
Babu, A. R. Suresh
Raghunathan, R.
[J]. TETRAHEDRON LETTERS, 2006, 47 (52) : 9221 - 9225
[7] Highly Enantioselective Synthesis of Propargyl Amides through Rh-Catalyzed Asymmetric Hydroalkynylation of Enamides: Scope, Mechanism, and Origin of Selectivity
Bai, Xiao-Yan
Zhang, Wen-Wen
Li, Qian
Li, Bi-Jie
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (01) : 506 - 514
[8] Ru(II)-Catalyzed C-H activation and annulation of salicylaldehydes with monosubstituted and disubstituted alkynes
Baruah, Swagata
Kaishap, Partha Pratim
Gogoi, Sanjib
[J]. CHEMICAL COMMUNICATIONS, 2016, 52 (88) : 13004 - 13007
[9] Rh(III)-catalyzed diastereoselective C-H bond addition/cyclization cascade of enone tethered aldehydes
Boerth, Jeffrey A.
Ellman, Jonathan A.
[J]. CHEMICAL SCIENCE, 2016, 7 (02) : 1474 - 1479
[10] Rhodium-Catalyzed, Remote Terminal Hydroarylation of Activated Olefins through a Long-Range Deconjugative Isomerization
Borah, Arun Jyoti
Shi, Zhuangzhi
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (19) : 6062 - 6066

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