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Graham Pattison

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Organization: University of Warwick , England
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Title: (PhD)
Transition-Metal-Free Homologative Cross-Coupling of Aldehydes and Ketones with Geminal Bis(boron) Compounds
Co-reporter:Thomas C. Stephens and Graham Pattison
Organic Letters July 7, 2017 Volume 19(Issue 13) pp:
Publication Date(Web):June 13, 2017
DOI:10.1021/acs.orglett.7b01474
We report a transition-metal-free coupling of aldehydes and ketones with geminal bis(boron) building blocks which provides the coupled, homologated carbonyl compound upon oxidation. This reaction not only extends an alkyl chain containing a carbonyl group, it also simultaneously introduces a new carbonyl substituent. We demonstrate that enantiopure aldehydes with an enolizable stereogenic center undergo this reaction with complete retention of stereochemistry.
One-pot synthesis of difluoromethyl ketones by a difluorination/fragmentation process
Co-reporter:Daniel J. Leng, Conor M. Black and Graham Pattison  
Organic & Biomolecular Chemistry 2016 vol. 14(Issue 5) pp:1531-1535
Publication Date(Web):16 Dec 2015
DOI:10.1039/C5OB02468D
Difluoromethyl ketones are an under-studied class of ketones which have great potential as useful building blocks for materials and drug design. Here we report a simple and convenient synthesis of this class of compounds via a one-pot difluorination/fragmentation of 1-trifluoromethyl-1,3-diketones which should now allow the chemistry of difluoromethyl ketones to be fully developed.
Apparent Electrophilic Fluorination of 1,3-Dicarbonyl Compounds Using Nucleophilic Fluoride Mediated by PhI(OAc)2
Co-reporter:Toby J. Nash
European Journal of Organic Chemistry 2015 Volume 2015( Issue 17) pp:3779-3786
Publication Date(Web):
DOI:10.1002/ejoc.201500370

Abstract

The apparent electrophilic fluorination of 1,3-dicarbonyl compounds using Et3N·3HF as a nucleophilic fluoride source is reported. This reaction requires PhI(OAc)2 as oxidant and can be conducted safely in standard laboratory glassware. Alternative selectivity compared to Selectfluor was observed in some cases. This approach may reduce our reliance on difficult-to-handle fluorine gas and expensive electrophilic fluorinating agents derived from elemental fluorine. Mechanistic analysis related to the active fluorinating species and fluoride/acetate exchange is presented.

One-pot synthesis of difluoromethyl ketones by a difluorination/fragmentation process
Co-reporter:Daniel J. Leng, Conor M. Black and Graham Pattison
Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 5) pp:NaN1535-1535
Publication Date(Web):2015/12/16
DOI:10.1039/C5OB02468D
Difluoromethyl ketones are an under-studied class of ketones which have great potential as useful building blocks for materials and drug design. Here we report a simple and convenient synthesis of this class of compounds via a one-pot difluorination/fragmentation of 1-trifluoromethyl-1,3-diketones which should now allow the chemistry of difluoromethyl ketones to be fully developed.
Rh-Catalyzed arylation of fluorinated ketones with arylboronic acids
Co-reporter:Luca S. Dobson and Graham Pattison
Chemical Communications 2016 - vol. 52(Issue 74) pp:NaN11119-11119
Publication Date(Web):2016/08/16
DOI:10.1039/C6CC05775F
The Rh-catalyzed arylation of fluorinated ketones with boronic acids is reported. This efficient process allows access to fluorinated alcohols in high yields under mild conditions. Competition experiments suggest that difluoromethyl ketones are more reactive than trifluoromethyl ketones in this process, despite their decreased electronic activation, an effect we postulate to be steric in origin.
Cyclopentanecarboxylic acid, 1-fluoro-2-oxo-, ethyl ester
Cyclopentanecarboxylic acid, 1-fluoro-2-oxo-, ethyl ester
CAS:84131-44-2
Cyclopentanecarboxylic acid, 1-fluoro-2-oxo-, ethyl ester
1,3-Butanedione, 2,2,4,4,4-pentafluoro-1-(2-thienyl)-
1,3-Butanedione, 2,2,4,4,4-pentafluoro-1-(2-thienyl)-
CAS:557114-02-0
1,3-Butanedione, 2,2,4,4,4-pentafluoro-1-(2-thienyl)-
2-Butanone, 1,1-difluoro-4-phenyl-
2-Butanone, 1,1-difluoro-4-phenyl-
CAS:145299-84-9
2-Butanone, 1,1-difluoro-4-phenyl-
Ethanone, 2,2-difluoro-1-(3-methylphenyl)- (9CI)
Ethanone, 2,2-difluoro-1-(3-methylphenyl)- (9CI)
CAS:50562-05-5
Ethanone, 2,2-difluoro-1-(3-methylphenyl)- (9CI)
ETHANONE, 1-(4-CHLOROPHENYL)-2,2-DIFLUORO-
ETHANONE, 1-(4-CHLOROPHENYL)-2,2-DIFLUORO-
CAS:655-54-9
ETHANONE, 1-(4-CHLOROPHENYL)-2,2-DIFLUORO-
Iodine, difluorophenyl-
Iodine, difluorophenyl-
CAS:26735-53-5
Iodine, difluorophenyl-
1H-Indene-1,3(2H)-dione, 2-fluoro-2-phenyl-
1H-Indene-1,3(2H)-dione, 2-fluoro-2-phenyl-
CAS:148433-42-5
1H-Indene-1,3(2H)-dione, 2-fluoro-2-phenyl-
2,4-Hexanedione, 1,1,1-trifluoro-6-phenyl-
2,4-Hexanedione, 1,1,1-trifluoro-6-phenyl-
CAS:1495-56-3
2,4-Hexanedione, 1,1,1-trifluoro-6-phenyl-
2-acetoxy-3-oxo-butanoic acid, ethyl ester
2-acetoxy-3-oxo-butanoic acid, ethyl ester
CAS:18632-42-3
2-acetoxy-3-oxo-butanoic acid, ethyl ester
Ethanone, 2,2-difluoro-1-(4-nitrophenyl)-
Ethanone, 2,2-difluoro-1-(4-nitrophenyl)-
CAS:860299-98-5
Ethanone, 2,2-difluoro-1-(4-nitrophenyl)-