Literature DB >> 23767882

Pd-catalyzed cross-coupling of potassium alkenyltrifluoroborates with 2-chloroacetates and 2-chloroacetamides.

Gary A Molander1, Thiago Barcellos, Kaitlin M Traister.   

Abstract

A protocol for the stereocontrolled synthesis of (E)- and (Z)-β,γ-unsaturated esters and amides is reported. 2-Chloroacetates as well as secondary and tertiary 2-chloroacetamides were successfully employed as electrophiles in the Suzuki-Miyaura cross-coupling reaction with potassium (E)- and (Z)-alkenyltrifluoroborates, affording the corresponding products in high yield.

Entities:  

Mesh：

Substances：

Year:  2013        PMID： 23767882      PMCID： PMC3737580          DOI： 10.1021/ol401377q

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


  17 in total

1.  Synthesis of Isotopically Labeled (E)-beta,gamma-Unsaturated Esters with Total or High Diastereoselectivity by Using Samarium Diiodide We thank II Plan Regional de Investigación del Principado de Asturias (PB-PGI98-04) and Ministerio de Educación y Cultura (PB97-1278) for financial support and Dr. Francisco J. González for valuable discussions. J.M.C. thanks Carmen Fernández for her collaboration. H.R.S. thanks the Principado de Asturias for a predoctoral fellowship.

Authors:  José M. Concellón; Pablo L. Bernad; Humberto Rodríguez-Solla
Journal:  Angew Chem Int Ed Engl       Date:  2001-10-15       Impact factor: 15.336

2.  cis-Apa: a practical linker for the microwave-assisted preparation of cyclic pseudopeptides via RCM cyclative cleavage.

Authors:  Alice Baron; Pascal Verdié; Jean Martinez; Frédéric Lamaty
Journal:  J Org Chem       Date:  2011-01-07       Impact factor: 4.354

Review 3.  Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors:  Sylvain Darses; Jean-Pierre Genet
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

4.  Catalytic asymmetric Hiyama cross-couplings of racemic alpha-bromo esters.

Authors:  Xing Dai; Neil A Strotman; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2008-02-27       Impact factor: 15.419

5.  Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

6.  A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

Authors:  Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

7.  Enantioselective alkenylation via nickel-catalyzed cross-coupling with organozirconium reagents.

Authors:  Sha Lou; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-04-14       Impact factor: 15.419

8.  Stereoselective Suzuki-Miyaura cross-coupling reactions of potassium alkenyltrifluoroborates with alkenyl bromides.

Authors:  Gary A Molander; Luciana A Felix
Journal:  J Org Chem       Date:  2005-05-13       Impact factor: 4.354

9.  One-pot synthesis of trisubstituted conjugated dienes via sequential Suzuki-Miyaura cross-coupling with alkenyl- and alkyltrifluoroborates.

Authors:  Gary A Molander; Yasuo Yokoyama
Journal:  J Org Chem       Date:  2006-03-17       Impact factor: 4.354

10.  Radical alkenylation of alpha-halo carbonyl compounds with alkenylindiums.

Authors:  Kazuaki Takami; Hideki Yorimitsu; Koichiro Oshima
Journal:  Org Lett       Date:  2004-11-25       Impact factor: 6.005
View more
  6 in total

1.  Synthesis of Amino-ADT Provides Access to Hydrolytically Stable Amide-Coupled Hydrogen Sulfide Releasing Drug Targets.

Authors:  Matthew D Hammers; Loveprit Singh; Leticia A Montoya; Alan D Moghaddam; Michael D Pluth
Journal:  Synlett       Date:  2016       Impact factor: 2.454

2.  Pd-catalyzed alkynylation of 2-chloroacetates and 2-chloroacetamides with potassium alkynyltrifluoroborates.

Authors:  Gary A Molander; Kaitlin M Traister
Journal:  Org Lett       Date:  2013-09-16       Impact factor: 6.005

3.  Alkenylation of C(sp3 )-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts.

Authors:  Chuan Liu; Qiu Wang
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-15       Impact factor: 15.336

4.  Direct catalytic cross-coupling of alkenyllithium compounds.

Authors:  Valentín Hornillos; Massimo Giannerini; Carlos Vila; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Sci       Date:  2014-11-28       Impact factor: 9.825

5.  First total synthesis of ampullosine, a unique isoquinoline alkaloid isolated from Sepedonium ampullosporum, and of the related permethylampullosine.

Authors:  Didier F Vargas; Enrique L Larghi; Teodoro S Kaufman
Journal:  RSC Adv       Date:  2019-10-16       Impact factor: 4.036

6.  Stereospecific Ni-catalyzed cross-coupling of potassium alkenyltrifluoroborates with alkyl halides.

Authors:  Gary A Molander; O Andreea Argintaru
Journal:  Org Lett       Date:  2014-03-25       Impact factor: 6.005
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.