Literature DB >> 20804186

Palladium-catalyzed carbonylative Heck-type reactions of alkyl iodides.

Kayla S Bloome1, Erik J Alexanian.   

Abstract

A palladium-catalyzed carbonylative Heck-type cyclization of alkyl halides is described. Treatment of a range of primary and secondary alkyl iodides with catalytic palladium(0) under CO pressure forms a variety of synthetically versatile enone products. The reactivity described represents a rare example of a palladium-catalyzed Heck-type cyclization involving unactivated alkyl halides with β-hydrogens. Alkene substitution is well tolerated, and mono- and bicyclic carbocycles may be easily accessed.

Entities:  

Year:  2010        PMID： 20804186     DOI： 10.1021/ja1053913

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


  17 in total

1.  Intercepting Wacker intermediates with arenes: C-H functionalization and dearomatization.

Authors:  Bryan S Matsuura; Allison G Condie; Ian A McBee; Ryan C Buff; Gregory J Karahalis; Corey R J Stephenson
Journal:  Org Lett       Date:  2011-11-09       Impact factor: 6.005

2.  Utilizing Carbonyl Coordination of Native Amides for Palladium-Catalyzed C(sp3 )-H Olefination.

Authors:  Hojoon Park; Yang Li; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-04       Impact factor: 15.336

3.  Palladium-catalyzed, ring-forming aromatic C-H alkylations with unactivated alkyl halides.

Authors:  Alexander R O Venning; Patrick T Bohan; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2015-03-16       Impact factor: 15.419

4.  Total syntheses of cyanthiwigins B, F, and G.

Authors:  John A Enquist; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2011-07-18       Impact factor: 5.236

5.  Nickel-Catalyzed C-Alkylation of Nitroalkanes with Unactivated Alkyl Iodides.

Authors:  Sina Rezazadeh; Vijayarajan Devannah; Donald A Watson
Journal:  J Am Chem Soc       Date:  2017-06-08       Impact factor: 15.419

6.  Pd(II)-catalyzed carbonylation of C(sp3)-H bonds: a new entry to 1,4-dicarbonyl compounds.

Authors:  Eun Jeong Yoo; Masayuki Wasa; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-11-17       Impact factor: 15.419

7.  Transition-Metal (Pd, Ni, Mn)-Catalyzed C-C Bond Constructions Involving Unactivated Alkyl Halides and Fundamental Synthetic Building Blocks.

Authors:  Megan R Kwiatkowski; Erik J Alexanian
Journal:  Acc Chem Res       Date:  2019-03-25       Impact factor: 22.384

8.  Catalytic Radical Domino Reactions in Organic Synthesis.

Authors:  Leanne J Sebren; James J Devery; Corey R J Stephenson
Journal:  ACS Catal       Date:  2014-02-07       Impact factor: 13.084

9.  Manganese-Catalyzed Carboacylations of Alkenes with Alkyl Iodides.

Authors:  Caitlin M McMahon; Matthew S Renn; Erik J Alexanian
Journal:  Org Lett       Date:  2016-08-09       Impact factor: 6.005

10.  Ligand-Enabled γ-C(sp(3))-H Olefination of Amines: En Route to Pyrrolidines.

Authors:  Heng Jiang; Jian He; Tao Liu; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2016-02-04       Impact factor: 15.419
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