An N-(acetoxy)phthalimide motif as a visible-light pro-photosensitizer in photoredox decarboxylative arylthiation

2016 ◽  
Vol 52 (87) ◽  
pp. 12909-12912 ◽  
Author(s):  
Yunhe Jin ◽  
Haijun Yang ◽  
Hua Fu
Keyword(s):  
Visible Light ◽  
Functional Groups ◽  
Room Temperature ◽  
Good Tolerance ◽  
Decarboxylative Coupling

An efficient visible-light photoredox decarboxylative coupling of N-(acetoxy)phthalimides with aryl thiols has been developed. The reaction was performed well at room temperature with good tolerance of functional groups. Importantly, the visible-light photoredox decarboxylative arylthiation did not need an added photocatalyst.

scholarly journals Palladium-Catalyzed Room Temperature Acylative Cross-Coupling of Activated Amides with Trialkylboranes

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2412 ◽  
Author(s):  
Weijia Shi ◽  
Gang Zou
Keyword(s):  
Functional Groups ◽  
Room Temperature ◽  
Cross Coupling ◽  
Methyl Tert Butyl Ether ◽  
Palladium Chloride ◽  
Butyl Ether ◽  
Good Tolerance ◽  
Palladium Catalyzed ◽  
Supported Palladium

A highly efficient acylative cross-coupling of trialkylboranes with activated amides has been effected at room temperature to give the corresponding alkyl ketones in good to excellent yields by using 1,3-bis(2,6-diisopropyl)phenylimidazolylidene and 3-chloropyridine co-supported palladium chloride, the PEPPSI catalyst, in the presence of K2CO3 in methyl tert-butyl ether. The scope and limitations of the protocol were investigated, showing good tolerance of acyl, cyano, and ester functional groups in the amide counterpart while halo group competed via the classical Suzuki coupling. The trialkylboranes generated in situ by hydroboration of olefins with BH3 or 9-BBN performed similarly to those separately prepared, making this protocol more practical.

Synthesis of 1,2-amino alcohols by decarboxylative coupling of amino acid derived α-amino radicals to carbonyl compounds via visible-light photocatalyst in water

2020 ◽  
Vol 22 (2) ◽  
pp. 336-341 ◽  
Author(s):  
Shulei Pan ◽  
Min Jiang ◽  
Jinjin Hu ◽  
Ruigang Xu ◽  
Xiaofei Zeng ◽  
...  
Keyword(s):  
Amino Acids ◽  
Visible Light ◽  
Carbonyl Compounds ◽  
Room Temperature ◽  
Coupling Reaction ◽  
Amino Alcohols ◽  
Visible Light Photocatalyst ◽  
Radical Coupling ◽  
Decarboxylative Coupling ◽  
Radical Coupling Reaction

A general and efficient visible-light photoredox-catalyzed decarboxylative radical coupling reaction of N-aryl amino acids with aldehydes or ketones for the synthesis of 1,2-amino alcohols in water at room temperature is described.

Visible-Light-Promoted C2 Trifluoromethylation of Quinoline N-Oxides

Synthesis ◽  
2019 ◽  
Vol 52 (02) ◽  
pp. 219-226 ◽  
Author(s):  
Ce Liang ◽  
Wang-Tao Zhuo ◽  
Yan-Ning Niu ◽  
Guo-Lin Gao
Keyword(s):  
Visible Light ◽  
Functional Groups ◽  
Room Temperature ◽  
Efficient Synthesis ◽  
Mechanistic Studies ◽  
Reaction Proceeds

A photoredox catalytic strategy has been described for the direct C2 trifluoromethylation of quinoline N-oxides. This reaction is compatible with a range of synthetically relevant functional groups for providing efficient synthesis of a variety of C2 trifluoromethyl quinoline N-oxides at room temperature. Mechanistic studies indicated that the reaction proceeds via a radical pathway.

Metal-Free Regioselective Alkylation of Imidazo[1,2-a]pyridines with N-Hydroxyphthalimide Esters under Organic Photoredox Catalysis

Synlett ◽  
2020 ◽  
Vol 31 (04) ◽  
pp. 363-368 ◽  
Author(s):  
Can Jin ◽  
Bin Sun ◽  
Tengwei Xu ◽  
Liang Zhang ◽  
Rui Zhu ◽  
...  
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Eosin Y ◽  
Photoredox Catalysis ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Regioselective Alkylation ◽  
Decarboxylative Coupling ◽  
Aliphatic Carboxylic Acids

A visible-light-induced direct C–H alkylation of imidazo[1,2-a]pyridines has been developed. It proceeds at room temperature by employing inexpensive Eosin Y as a photocatalyst and alkyl N-hydroxyphthalimide (NHP) esters as alkylation reagents. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) were tolerated in this protocol, giving the corresponding C-5-alkylated products in moderate to excellent yields. Mechanistic studies indicate that a radical decarboxylative coupling pathway was involved in this process.

[3+2] Cycloaddition of N-Aminopyridines and Perfluoroalkynylphosphonates: Facile Synthesis of Perfluoroalkylated Pyrazolo[1,5-a]pyridines Containing a Phosphonate Moiety

Synthesis ◽  
2018 ◽  
Vol 50 (18) ◽  
pp. 3731-3737 ◽  
Author(s):  
Hui Zhang ◽  
Weiguo Cao ◽  
Qi Huang ◽  
Dong He ◽  
Jing Han ◽  
...  
Keyword(s):  
Functional Groups ◽  
Room Temperature ◽  
Pyridine Derivatives ◽  
Facile Synthesis ◽  
Good Tolerance ◽  
Phosphonate Group ◽  
Salient Features ◽  
Operational Simplicity

1,3-Zwitterions generated from N-aminopyridines in the presence of base are trapped by perfluoroalkynylphosphonates to yield a variety of perfluoroalkylated pyrazolo[1,5-a]pyridine derivatives bearing a phosphonate group. The salient features of these [3+2] cycloadditions include operational simplicity, good tolerance of functional groups, and good to excellent yields at room temperature.

Synthesis of N-Arylsulfonamides by a Copper-Catalyzed Reaction of Chloramine-T and Arylboronic Acids at Room Temperature

Synlett ◽  
2017 ◽  
Vol 29 (01) ◽  
pp. 111-115 ◽  
Author(s):  
Banlai Ouyang ◽  
Guanyinsheng Qiu ◽  
Deming Liu ◽  
Kejian Xia ◽  
Yanxia Zheng ◽  
...  
Keyword(s):  
Functional Groups ◽  
Related Compound ◽  
Room Temperature ◽  
Arylboronic Acid ◽  
Good Tolerance ◽  
Arylboronic Acids ◽  
Chloramine T

A copper-catalyzed Chan–Lam-coupling-like reaction of a (het)arylboronic acid and chloramine-T (or a related compound) has been developed for the synthesis of N-arylsulfonamides at room temperature in moderate to good yields, with good tolerance of functional groups. In this process, it is believed that chloramine-T serves as an electrophile.

Palladium-Catalyzed Decarboxylative Coupling Reactions of Propiolic Acid Derivatives and Arylsulfonyl Hydrazide

Synthesis ◽  
2018 ◽  
Vol 50 (16) ◽  
pp. 3197-3204 ◽  
Author(s):  
Kwang Song ◽  
Sunwoo Lee ◽  
Jaerim Park
Keyword(s):  
Functional Groups ◽  
Coupling Reaction ◽  
Coupling Reactions ◽  
Good Tolerance ◽  
Decarboxylative Coupling ◽  
Palladium Catalyzed ◽  
Propiolic Acid

Arylsulfonyl hydrazides were employed as coupling partners for the decarboxylative coupling reaction of propiolic acid derivatives. When the reaction was conducted using Pd(TFA)2 (1.0 mol%), dppp (1.0 mol%), and Cu(OAc)2 (2.4 equiv) in DMF at 100 °C for 0.5 hour, the desired coupled products were formed in moderate to good yields. The reaction showed good tolerance toward functional groups such as ester, ketone, cyano, nitro, chloro, and bromo groups.

Visible Light-Promoted Catalytic Ring-Opening Isomerization of 1,2-Disubstituted Cyclopropanols to Linear Ketones

2019 ◽  
Author(s):  
Marharyta V. Laktsevich-Iskryk ◽  
Nastassia A. Varabyeva ◽  
Volha V. Kazlova ◽  
Vladimir N. Zhabinskii ◽  
Vladimir A. Khripach ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Groups ◽  
Ring Opening ◽  
Radical Intermediates ◽  
Reaction Proceeds

In this article, we report a photocatalytic protocol for the isomerization of 1,2-disubstituted cyclopropanols to linear ketones. The reaction proceeds <i>via</i> radical intermediates and tolerates various functional groups.

Visible Light-Promoted Catalytic Ring-Opening Isomerization of 1,2-Disubstituted Cyclopropanols to Linear Ketones

2019 ◽  
Author(s):  
Marharyta V. Laktsevich-Iskryk ◽  
Nastassia A. Varabyeva ◽  
Volha V. Kazlova ◽  
Vladimir N. Zhabinskii ◽  
Vladimir A. Khripach ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Groups ◽  
Ring Opening ◽  
Radical Intermediates ◽  
Reaction Proceeds

In this article, we report a photocatalytic protocol for the isomerization of 1,2-disubstituted cyclopropanols to linear ketones. The reaction proceeds <i>via</i> radical intermediates and tolerates various functional groups.

Visible Light-Mediated Oxidative Debenzylation

2020 ◽  
Author(s):  
Cristian Cavedon ◽  
Eric T. Sletten ◽  
Amiera Madani ◽  
Olaf Niemeyer ◽  
Peter H. Seeberger ◽  
...  
Keyword(s):  
Reaction Time ◽  
Visible Light ◽  
Functional Groups ◽  
Continuous Flow ◽  
Protecting Groups ◽  
Benzyl Ether ◽  
Complex Molecules ◽  
Protective Groups ◽  
Benzyl Ethers ◽  
Harsh Conditions

Protecting groups are key in the synthesis of complex molecules such as carbohydrates to distinguish functional groups of similar reactivity. The harsh conditions required to cleave stable benzyl ether protective groups are not compatible with many other protective and functional groups. The mild, visible light-mediated debenzylation disclosed here renders benzyl ethers orthogonal protective groups. Key to success is the use of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as stoichiometric or catalytic photooxidant such that benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time for this transformation can be reduced from hours to minutes in continuous flow. <br>

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