Literature DB >> 23105962

A Copper-Catalyzed Arylation of Tryptamines for the Direct Synthesis of Aryl Pyrroloindolines.

Madeleine E Kieffer1, Kangway V Chuang, Sarah E Reisman.   

Abstract

An operationally simple, copper-catalyzed arylation of N-tosyltryptamines provides direct access to C3-aryl pyrroloindolines. A range of electron-donating and electron-withdrawing substituents is tolerated on both the indole backbone and the aryl electrophile. These reactions occur under ambient temperatures and with equimolar quantities of the coupling partners.

Entities:  

Year:  2012        PMID： 23105962      PMCID： PMC3480223          DOI： 10.1039/C2SC20914D

Source DB:  PubMed          Journal:  Chem Sci        ISSN： 2041-6520            Impact factor:   9.825


  36 in total

1.  Pd-catalyzed C3-selective allylation of indoles with allyl alcohols promoted by triethylborane.

Authors:  Masanari Kimura; Makoto Futamata; Ryutaro Mukai; Yoshinao Tamaru
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

2.  Room temperature and phosphine free palladium catalyzed direct C-2 arylation of indoles.

Authors:  Nathalie Lebrasseur; Igor Larrosa
Journal:  J Am Chem Soc       Date:  2008-02-16       Impact factor: 15.419

3.  Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes.

Authors:  Barry M Trost; Jean Quancard
Journal:  J Am Chem Soc       Date:  2006-05-17       Impact factor: 15.419

4.  Palladium-catalyzed C3-benzylation of indoles.

Authors:  Ye Zhu; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2011-12-09       Impact factor: 15.419

5.  Cyclopropylazetoindolines as precursors to C(3)-quaternary-substituted indolines.

Authors:  Vinson R Espejo; Xi-Bo Li; Jon D Rainier
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

6.  Copper-catalyzed aerobic oxidative functionalization of an arene C-H bond: evidence for an aryl-copper(III) intermediate.

Authors:  Amanda E King; Lauren M Huffman; Alicia Casitas; Miquel Costas; Xavi Ribas; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

7.  Total synthesis of (+)-11,11'-dideoxyverticillin A.

Authors:  Justin Kim; James A Ashenhurst; Mohammad Movassaghi
Journal:  Science       Date:  2009-04-10       Impact factor: 47.728

8.  Elements of regiocontrol in palladium-catalyzed oxidative arene cross-coupling.

Authors:  David R Stuart; Elisia Villemure; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2007-09-19       Impact factor: 15.419

9.  Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions.

Authors:  Robert J Phipps; Neil P Grimster; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2008-06-11       Impact factor: 15.419

10.  Total synthesis of (+/-)-psychotrimine.

Authors:  Timothy Newhouse; Phil S Baran
Journal:  J Am Chem Soc       Date:  2008-07-26       Impact factor: 15.419
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  9 in total

1.  Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

Authors:  Richard P Loach; Owen S Fenton; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419

2.  Enantioselective Synthesis of Pyrroloindolines via Noncovalent Stabilization of Indole Radical Cations and Applications to the Synthesis of Alkaloid Natural Products.

Authors:  Emily C Gentry; Lydia J Rono; Martina E Hale; Rei Matsuura; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2018-02-21       Impact factor: 15.419

3.  Natural products as inspiration for the development of new synthetic methods.

Authors:  Zhiqiang Ma; Chuo Chen
Journal:  J Chin Chem Soc       Date:  2017-08-09       Impact factor: 1.967

4.  Copper-catalyzed diastereoselective arylation of tryptophan derivatives: total synthesis of (+)-naseseazines A and B.

Authors:  Madeleine E Kieffer; Kangway V Chuang; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2013-04-03       Impact factor: 15.419

5.  Chiral anion phase transfer of aryldiazonium cations: an enantioselective synthesis of C3-diazenated pyrroloindolines.

Authors:  Hosea M Nelson; Solomon H Reisberg; Hunter P Shunatona; Jigar S Patel; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-08       Impact factor: 15.336

6.  Concise Total Synthesis of (+)-Luteoalbusins A and B.

Authors:  Timothy C Adams; Joshua N Payette; Jaime H Cheah; Mohammad Movassaghi
Journal:  Org Lett       Date:  2015-08-25       Impact factor: 6.005

7.  Concise Total Synthesis of (+)-Bionectins A and C.

Authors:  Alexis Coste; Justin Kim; Timothy C Adams; Mohammad Movassaghi
Journal:  Chem Sci       Date:  2013-08       Impact factor: 9.825

8.  C-H arylation of triphenylene, naphthalene and related arenes using Pd/C.

Authors:  Karl D Collins; Roman Honeker; Suhelen Vásquez-Céspedes; Dan-Tam D Tang; Frank Glorius
Journal:  Chem Sci       Date:  2014-12-22       Impact factor: 9.825

9.  Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade.

Authors:  James A Rossi-Ashton; Aimee K Clarke; Richard J K Taylor; William P Unsworth
Journal:  Org Lett       Date:  2020-01-15       Impact factor: 6.005
  9 in total

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