Literature DB >> 23427905

Palladium-catalyzed decarboxylative allylation and benzylation of N-alloc and N-Cbz indoles.

Thomas D Montgomery1, Ye Zhu, Natsuko Kagawa, Viresh H Rawal.   

Abstract

A set of general methods for the palladium-catalyzed decarboxylative C3-allylation and C3-benzylation of indoles, starting from the corresponding N-alloc and N-Cbz indoles, respectively, is reported. This chemistry provides ready access to a wide range of functionalized indolenines in good to excellent yields. A tandem process, wherein the palladium catalyzed allylation chemistry is coupled with a Mizoroki-Heck reaction, offers a simple route to cinnamylated products.

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Year:  2013        PMID: 23427905      PMCID: PMC3980966          DOI: 10.1021/ol400334u

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  23 in total

1.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Synthesis and functionalization of indoles through palladium-catalyzed reactions.

Authors:  Sandro Cacchi; Giancarlo Fabrizi
Journal:  Chem Rev       Date:  2005-07       Impact factor: 60.622

3.  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

4.  Enantioselective Pd-catalyzed allylic alkylation of indoles by a new class of chiral ferrocenyl P/S ligands.

Authors:  Hong Yee Cheung; Wing-Yiu Yu; Fuk Loi Lam; Terry T-L Au-Yeung; Zhongyuan Zhou; Tak Hang Chan; Albert S C Chan
Journal:  Org Lett       Date:  2007-09-13       Impact factor: 6.005

5.  Ir-catalyzed regio- and enantioselective Friedel-Crafts-type allylic alkylation of indoles.

Authors:  Wen-Bo Liu; Hu He; Li-Xin Dai; Shu-Li You
Journal:  Org Lett       Date:  2008-04-03       Impact factor: 6.005

6.  Ruthenium(IV) complexes featuring P,O-chelating ligands: regioselective substitution directly from allylic alcohols.

Authors:  Basker Sundararaju; Mathieu Achard; Bernard Demerseman; Loic Toupet; Gangavaram V M Sharma; Christian Bruneau
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-01       Impact factor: 15.336

7.  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

8.  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

9.  New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic substitution: controlling the regioselectivity.

Authors:  Marco Bandini; Alfonso Melloni; Achille Umani-Ronchi
Journal:  Org Lett       Date:  2004-09-02       Impact factor: 6.005

10.  Palladium-catalyzed beta-allylation of 2,3-disubstituted indoles.

Authors:  Natsuko Kagawa; Jeremiah P Malerich; Viresh H Rawal
Journal:  Org Lett       Date:  2008-05-21       Impact factor: 6.005

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  11 in total

1.  Friedel-Crafts Alkylation of Indoles with Trichloroacetimidates.

Authors:  Tamie Suzuki; John D Chisholm
Journal:  Tetrahedron Lett       Date:  2019-04-03       Impact factor: 2.415

2.  Synthesis of 3,3'-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates.

Authors:  Arijit A Adhikari; Léa Radal; John D Chisholm
Journal:  Synlett       Date:  2017-07-11       Impact factor: 2.454

Review 3.  Recent advances in the development of polycyclic skeletons via Ugi reaction cascades.

Authors:  Jie Lei; Jiang-Ping Meng; Dian-Yong Tang; Brendan Frett; Zhong-Zhu Chen; Zhi-Gang Xu
Journal:  Mol Divers       Date:  2018-01-16       Impact factor: 2.943

4.  α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction.

Authors:  Mayavan Viji; Manjunatha Vishwanath; Jaeuk Sim; Yunjeong Park; Chanhyun Jung; Seohu Lee; Heesoon Lee; Kiho Lee; Jae-Kyung Jung
Journal:  RSC Adv       Date:  2020-10-07       Impact factor: 4.036

5.  Highly efficient synthesis and stereoselective migration reactions of chiral five-membered aza-spiroindolenines: scope and mechanistic understanding.

Authors:  Qing-Feng Wu; Chao Zheng; Chun-Xiang Zhuo; Shu-Li You
Journal:  Chem Sci       Date:  2016-03-29       Impact factor: 9.825

6.  Platinum-Catalyzed Allylation of 2,3-Disubstituted Indoles with Allylic Acetates.

Authors:  Bai-Jing Peng; Wen-Ting Wu; And Shyh-Chyun Yang
Journal:  Molecules       Date:  2017-11-29       Impact factor: 4.411

7.  Organophotoredox/palladium dual catalytic decarboxylative Csp3-Csp3 coupling of carboxylic acids and π-electrophiles.

Authors:  Kaitie C Cartwright; Jon A Tunge
Journal:  Chem Sci       Date:  2020-07-16       Impact factor: 9.825

8.  Rapid assembly of functionalised spirocyclic indolines by palladium-catalysed dearomatising diallylation of indoles with allyl acetate.

Authors:  Persis Dhankher; Laure Benhamou; Tom D Sheppard
Journal:  Chemistry       Date:  2014-08-29       Impact factor: 5.236

9.  Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate.

Authors:  Thomas D Montgomery; Antoinette E Nibbs; Ye Zhu; Viresh H Rawal
Journal:  Org Lett       Date:  2014-06-25       Impact factor: 6.005

10.  Palladium-Catalyzed Modular Synthesis of Substituted Piperazines and Related Nitrogen Heterocycles.

Authors:  Thomas D Montgomery; Viresh H Rawal
Journal:  Org Lett       Date:  2016-01-29       Impact factor: 6.005

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