Literature DB >> 15584721

A unique catalyst effects the rapid room-temperature cross-coupling of organozinc reagents with carboxylic acid fluorides, chlorides, anhydrides, and thioesters.

Yongda Zhang1, Tomislav Rovis.   

Abstract

We have identified a catalyst capable of effecting the rapid, room-temperature cross-coupling between acid fluorides and diorganozinc reagents. The use of acid fluorides as electrophilic partners allows this reaction to tolerate epimerizable functionality as well as beta leaving groups. The same catalyst is also capable of cross-coupling acid chlorides, acyl cyanides, anhydrides, thioesters, and pyridyl esters. Noteworthy is the ability of the reaction to successfully transfer both groups from the organometalic fragment.

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Year:  2004        PMID: 15584721     DOI: 10.1021/ja044113k

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  20 in total

1.  Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9-BBN-Derived Ate Complexes.

Authors:  Chunyin Law; Yan Meng; Seung Moh Koo; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2019-04-04       Impact factor: 15.336

2.  Synthesis of functionalized dialkyl ketones from carboxylic acid derivatives and alkyl halides.

Authors:  Alexander C Wotal; Daniel J Weix
Journal:  Org Lett       Date:  2012-02-23       Impact factor: 6.005

3.  Breaking Amides using Nickel Catalysis.

Authors:  Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084

4.  Nickel-Catalyzed Alkylation of Amide Derivatives.

Authors:  Bryan J Simmons; Nicholas A Weires; Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2016-04-12       Impact factor: 13.084

5.  Development of a Modular Synthetic Route to (+)-Pleuromutilin, (+)-12-epi-Mutilins, and Related Structures.

Authors:  Mingshuo Zeng; Stephen K Murphy; Seth B Herzon
Journal:  J Am Chem Soc       Date:  2017-11-02       Impact factor: 15.419

6.  Application of the McMurry coupling reaction in the synthesis of tri- and tetra-arylethylene analogues as potential cancer chemotherapeutic agents.

Authors:  Rajendra P Tanpure; Amanda R Harkrider; Tracy E Strecker; Ernest Hamel; Mary Lynn Trawick; Kevin G Pinney
Journal:  Bioorg Med Chem       Date:  2009-08-12       Impact factor: 3.641

7.  Ambient temperature synthesis of high enantiopurity N-protected peptidyl ketones by peptidyl thiol ester-boronic acid cross-coupling.

Authors:  Hao Yang; Hao Li; Rüdiger Wittenberg; Masahiro Egi; Wenwei Huang; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2007-02-07       Impact factor: 15.419

8.  Nickel-Catalyzed Synthesis of Ketones from Alkyl Halides and Acid Chlorides: Preparation of Ethyl 4-Oxododecanoate.

Authors:  Alexander C Wotal; Donald C Batesky; Daniel J Weix
Journal:  Organic Synth       Date:  2016-02-22

9.  A copper-catalyzed, pH-neutral construction of high-enantiopurity peptidyl ketones from peptidic s-acylthiosalicylamides in air at room temperature.

Authors:  Lanny S Liebeskind; Hao Yang; Hao Li
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Palladium-catalyzed reactions of arylindium reagents prepared directly from aryl iodides and indium metal.

Authors:  Vardan Papoian; Thomas Minehan
Journal:  J Org Chem       Date:  2008-08-22       Impact factor: 4.354

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