Literature DB >> 35416212

Generation of formaldehyde and formaldehyde-d2 for hydroxymethylations and hydroxydeuteromethylations of difluoroenolates and difluorobenzyl carbanions.

Hari R Khatri1, Changho Han2, Reem A Alkhodier1, Amna T Adam1, Baharul Islam1, David A Colby1.   

Abstract

A method for the in situ production of formaldehyde from dimethylsulfoxide, bromine, and cesium carbonate is reported for reactions with difluoroenolates and difluorobenzyl carbanions. This process also generates formaldehyde-d2 for the production of 2,2-difluoro-1,1-deuteroethanols. Mechanistic and computational studies further characterize the production of hydroxymethylated and hydroxydeuteromethylated difluorinated organic molecules.

Entities:  

Mesh：

Substances：

Year:  2022        PMID： 35416212      PMCID： PMC9205602          DOI： 10.1039/d2cc01518h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.065


  25 in total

1.  Catalytic Regioselective γ-Methylenation of α,β-Unsaturated Aldehydes Using Formaldehyde via Vinylogous Aldol Condensation.

Authors:  Mahesh S Kutwal; Sachin Dev; Chandrakumar Appayee
Journal:  Org Lett       Date:  2019-04-02       Impact factor: 6.005

2.  Deuteriodifluoromethylation and gem-Difluoroalkenylation of Aldehydes Using ClCF2 H in Continuous Flow.

Authors:  Wai Chung Fu; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-04       Impact factor: 15.336

3.  Ru(II)-Catalyzed Regioselective Hydroxymethylation of β-Carbolines and Isoquinolines via C-H Functionalization: Probing the Mechanism by Online ESI-MS/MS Screening.

Authors:  Ramya Tokala; Darshana Bora; Sravani Sana; Fabiane M Nachtigall; Leonardo S Santos; Nagula Shankaraiah
Journal:  J Org Chem       Date:  2019-04-16       Impact factor: 4.354

4.  Conversion of Methyl Ketones and Methyl Sulfones into α-Deutero-α,α-Difluoromethyl Ketones and α-Deutero-α,α-Difluoromethyl Sulfones in Three Synthetic Steps.

Authors:  Munia F Sowaileh; Changho Han; Robert A Hazlitt; Eun Hoo Kim; Jinu P John; David A Colby
Journal:  Tetrahedron Lett       Date:  2016-12-21       Impact factor: 2.415

5.  Selective Conversion of Carbon Dioxide to Formaldehyde via a Bis(silyl)acetal: Incorporation of Isotopically Labeled C1 Moieties Derived from Carbon Dioxide into Organic Molecules.

Authors:  Michael Rauch; Zack Strater; Gerard Parkin
Journal:  J Am Chem Soc       Date:  2019-10-22       Impact factor: 15.419

Review 6.  Deuterium- and Tritium-Labelled Compounds: Applications in the Life Sciences.

Authors:  Jens Atzrodt; Volker Derdau; William J Kerr; Marc Reid
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-04       Impact factor: 15.336

7.  Magnesium-Promoted Additions of Difluoroenolates to Unactivated Imines.

Authors:  Alex L Nguyen; Hari R Khatri; James R Woods; Cassidy S Baldwin; Frank R Fronczek; David A Colby
Journal:  J Org Chem       Date:  2018-02-27       Impact factor: 4.354

8.  Base-Catalyzed H/D Exchange Reaction of Difluoromethylarenes.

Authors:  Linwei Huang; Wei Liu; Liang-Liang Zhao; Zengyu Zhang; Xiaoyu Yan
Journal:  J Org Chem       Date:  2021-02-16       Impact factor: 4.354

9.  Catalytic enantioselective difluoroalkylation of aldehydes.

Authors:  Peng Zhang; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-18       Impact factor: 15.336

10.  Discovery of Dosimertinib, a Highly Potent, Selective, and Orally Efficacious Deuterated EGFR Targeting Clinical Candidate for the Treatment of Non-Small-Cell Lung Cancer.

Authors:  Yonggang Meng; Bin Yu; He Huang; Youmei Peng; Ertong Li; Yongfang Yao; Chuanjun Song; Wenquan Yu; Kaikai Zhu; Kai Wang; Dongxu Yi; Jinfa Du; Junbiao Chang
Journal:  J Med Chem       Date:  2021-01-18       Impact factor: 7.446
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.