Easy access to secondary and tertiary alcohols via metal-free and light mediated radical carbonyl allylation

2021 ◽  
Vol 57 (82) ◽  
pp. 10783-10786
Author(s):  
Benjamin Rui Peng Yip ◽  
Kumar Bhaskar Pal ◽  
Junjie Desmond Lin ◽  
Yuan Xu ◽  
Mrinmoy Das ◽  
...  
Keyword(s):  
Easy Access ◽  
Metal Free ◽  
Tertiary Alcohols ◽  
Aryl Ketones ◽  
Carbonyl Allylation

An organo-photocatalyst catalyzed allylation of aryl ketones and aldehydes using readily available unactivated allylic substrates has been reported.

Metal-Free Photoinduced Transformation of Aryl Halides and Diketones into Aryl Ketones

2019 ◽  
Vol 2019 (16) ◽  
pp. 2721-2724 ◽  
Author(s):  
Qiuli Yao ◽  
Wenbo Liu ◽  
Peng Liu ◽  
Linjing Ren ◽  
Xuehong Fang ◽  
...  
Keyword(s):  
Aryl Halides ◽  
Metal Free ◽  
Aryl Ketones ◽  
Photoinduced Transformation

scholarly journals Easy Access to Allylic Sulfones Through Transition-Metal-Free Hydrosulfonylation Of Allenes

2021 ◽  
Author(s):  
Lucas Pagès ◽  
Sébastien Lemouzy ◽  
Marc Taillefer ◽  
Florian Monnier
Keyword(s):  
Transition Metal ◽  
Easy Access ◽  
Metal Free

Metal-free synthesis of 3-chalcogenyl chromones from alkynyl aryl ketones and diorganyl diselenides/disulfides mediated by PIFA

2020 ◽  
Vol 7 (23) ◽  
pp. 3935-3940
Author(s):  
Zhenkang Ai ◽  
Jiaxi Xiao ◽  
Yadong Li ◽  
Boying Guo ◽  
Yunfei Du ◽  
...  
Keyword(s):  
Metal Free ◽  
Aryl Ketones

3-Selenyl/sulfenyl chromones/thiochromones were conveniently synthesized from the PIFA-mediated reactions between alkynyl aryl ketones bearing an ortho-methoxy/methylthio group and diorganyl diselenides/disulfides.

Metal-Free Synthesis of 2,4,6-Trisubstituted Pyridines via Iodine-Initiated Reaction of Methyl Aryl Ketones with Amines under Neat Heating

Synthesis ◽  
2016 ◽  
Vol 49 (08) ◽  
pp. 1879-1883 ◽  
Author(s):  
Ze Zhang ◽  
Hui Xu ◽  
Ji-Chao Zeng ◽  
Fang-Jian Wang
Keyword(s):  
Metal Free ◽  
Aryl Ketones

ChemInform Abstract: Transition-Metal-Free α-Arylation of Enolizable Aryl Ketones and Mechanistic Evidence for a Radical Process.

ChemInform ◽  
2016 ◽  
Vol 47 (4) ◽  
pp. no-no
Author(s):  
Martin Pichette Drapeau ◽  
Indira Fabre ◽  
Laurence Grimaud ◽  
Ilaria Ciofini ◽  
Thierry Ollevier ◽  
...  
Keyword(s):  
Transition Metal ◽  
Radical Process ◽  
Metal Free ◽  
Aryl Ketones

Visible light-promoted umpolung coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines

2018 ◽  
Vol 54 (78) ◽  
pp. 11017-11020 ◽  
Author(s):  
Xiao Xu ◽  
Qing-Qiang Min ◽  
Na Li ◽  
Feng Liu
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Light Irradiation ◽  
Metal Free ◽  
Tertiary Alcohols ◽  
Simple Protocol

A metal-free, mild, and simple protocol is developed for the synthesis of tertiary alcohols bearing tri-/difluoromethyl groups upon visible-light irradiation.

scholarly journals General and selective deoxygenation by hydrogen using a reusable earth-abundant metal catalyst

2019 ◽  
Vol 5 (11) ◽  
pp. eaav3680 ◽  
Author(s):  
T. Schwob ◽  
P. Kunnas ◽  
N. de Jonge ◽  
C. Papp ◽  
H.-P. Steinrück ◽  
...  
Keyword(s):  
Natural Products ◽  
Hydrogen Gas ◽  
Metal Catalyst ◽  
Tertiary Alcohols ◽  
Aryl Ketones ◽  
Earth Abundant ◽  
Fuels And Chemicals ◽  
Cost Efficient ◽  
Economic Upgrading ◽  
Selective Deoxygenation

Chemoselective deoxygenation by hydrogen is particularly challenging but crucial for an efficient late-stage modification of functionality-laden fine chemicals, natural products, or pharmaceuticals and the economic upgrading of biomass-derived molecules into fuels and chemicals. We report here on a reusable earth-abundant metal catalyst that permits highly chemoselective deoxygenation using inexpensive hydrogen gas. Primary, secondary, and tertiary alcohols as well as alkyl and aryl ketones and aldehydes can be selectively deoxygenated, even when part of complex natural products, pharmaceuticals, or biomass-derived platform molecules. The catalyst tolerates many functional groups including hydrogenation-sensitive examples. It is efficient, easy to handle, and conveniently synthesized from a specific bimetallic coordination compound and commercially available charcoal. Selective, sustainable, and cost-efficient deoxygenation under industrially viable conditions seems feasible.

Iodine- and TBHP-Promoted Acylation of Benzothiazoles under Metal-Free Conditions

Synthesis ◽  
2020 ◽  
Author(s):  
Keyume Ablajan ◽  
Bin Wang ◽  
Qianwei Zhang ◽  
Zhongqi Guo
Keyword(s):  
Ring Opening ◽  
Amino Group ◽  
Metal Free ◽  
Product Yields ◽  
Broad Scope ◽  
Simple Protocol ◽  
Aryl Ketones ◽  
Aryl Ketone

A simple protocol for the synthesis of 2-acylbenzothiazoles using aryl ketones and benzothiazoles in the presence of I2 and TBHP is described. Acylation of the benzothiazoles is achieved through a sequence involving oxidation of the aryl ketone to an aryl glyoxal, ring-opening of the benzothiazole followed by condensation of the amino group with the aryl glyoxal, cyclization and oxidation. The method avoids the use of metals and toxic solvents. In addition, this protocol has the advantage of broad scope and provides good to excellent product yields.

Iodinane- and Metal-Free Synthesis ofN-Cyano Sulfilimines:  Novel and Easy Access ofNH-Sulfoximines

2007 ◽  
Vol 9 (19) ◽  
pp. 3809-3811 ◽  
Author(s):  
Olga García Mancheño ◽  
Olivia Bistri ◽  
Carsten Bolm
Keyword(s):  
Easy Access ◽  
Metal Free

scholarly journals α-Acetoxyarone synthesis via iodine-catalyzed and tert-butyl hydroperoxide-mediateded self-intermolecular oxidative coupling of aryl ketones

2017 ◽  
Vol 13 ◽  
pp. 1079-1084 ◽  
Author(s):  
Liquan Tan ◽  
Cui Chen ◽  
Weibing Liu
Keyword(s):  
Oxidative Coupling ◽  
Optimum Conditions ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Radical Intermediates ◽  
Tert Butyl Hydroperoxide ◽  
Aryl Ketones

We present a metal-free method for α-acetoxyarone synthesis by self-intermolecular oxidative coupling of aryl ketones using I2−tert-butyl hydroperoxide (TBHP). Under the optimum conditions, various aryl ketones gave the corresponding products in moderate to excellent yields. A series of control experiments were performed; the results suggest the involvement of radical pathways. Multiple radical intermediates were generated in situ and the overall process involved several different reactions, which proceeded self-sequentially in a single reactor. A labeling experiment using 18O-labeled H2O confirmed that the oxygen in the product was derived from TBHP, not from H2O in the TBHP solvent.

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