Palladium-Catalyzed Heck-type Domino Cyclization and Carboxylation to Synthesize Carboxylic Acids by Utilizing Chloroform as the Carbon Monoxide Source

Liu, Xianglei; Li, Bin; Gu, Zhenhua

doi:10.1021/acs.joc.5b01126

Cited by 64 publications

(23 citation statements)

References 73 publications

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“…To circumvent the issue of handling gaseous carbon monoxide, a variety of solid and liquid CO precursors have been used for the installing the CO moiety. [42][43][44][45][46][47][48][49][50][51] However, only few of the CO precursors can acts as C1 source for the carbonylative Suzuki-Miyaura reaction. Recent approaches involve the ex situ generation of CO from an organic precursor, such as a formic acid [52] and chloroform.…”

Section: Full Papersmentioning

confidence: 99%

Dppf‐Ligated Palladium Complex as an Efficient Catalyst for the Synthesis of Biaryl Ketones Using Co₂(CO)₈ as a C1 Source with High TON and TOF

et al. 2019

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In this reports, we have synthesized and characterized the palladium catalyst [Pd2(dppf)2(SC12H8S)]2(OTf)4 which is successfully applied for Carbonylative Suzuki‐Miyaura cross‐coupling reaction. Synthesized catalyst was characterized by various analytical techniques such as 1H NMR, 31P NMR, CHNS, and single crystal X‐ray diffraction. The use of Co2(CO)8 as a C1 source instead of gaseous CO is an additional advantage of the developed protocol. The current protocol showing excellent catalytic activity at ppm level of “Pd” concentration to provided high TON and TON. TON could be achieved up to 104 and TOF up to 103. The protocol could tolerate a variety of functional groups and provided wide substrate scope including Heteroaryl ketones. The practical applicability of the proposed protocol up to gram level with marginal loss of the yield of the product. Remarkably, we have synthesized (4‐methoxyphenyl) (3,4,5‐trimethoxyphenyl)methanone and oxybenzone which is pharmaceutically active drug molecules under co‐catalyst, and additive free condition. .

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Section: Full Papersmentioning

confidence: 99%

Dppf‐Ligated Palladium Complex as an Efficient Catalyst for the Synthesis of Biaryl Ketones Using Co₂(CO)₈ as a C1 Source with High TON and TOF

et al. 2019

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“…In 2015, Gu et al reported an innovative sequence involving a cyclocarbopalladation followed by in situ hydrocarboxylation using CHCl 3 as a 'CO' source. 66 Once the 5exo-trig Heck-type cyclization has taken place, the resulting palladium-hydride species can add to the newly formed C-C double bond to form the isomer of intermediate 110 that can subsequently react with chloroform to give the target compound 111 (Scheme 33). Additionally, this strategy has been applied to cascade reactions ending with a hydromethenylation using hydrazones as coupling partners.…”

Section: Scheme 32 Cascade Reaction Involving a Cyclocarbopalladationmentioning

confidence: 99%

Cyclocarbopalladation as a Key Step in Cascade Reactions: Recent Developments

et al. 2017

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Cascade reactions are step-economical processes for the synthesis of complex molecules as they allow, in one step, the formation of multiple bonds. Over the last two decades cyclocarbopalladation has emerged as a powerful key step when integrated into these sequences and has allowed unprecedented valuable polycyclic scaffolds to be obtained. This review is focused on recent developments in this field including original cascade sequences, novel activation modes (C-H activation for instance) and unprecedented families of substrates. 1 Introduction 2 Formation of Carbocycles 2.1 4-exo Cyclocarbopalladation 2.2 5-exo Cyclocarbopalladation 2.3 5-endo Cyclocarbopalladation 2.4 Cyclocarbopalladation with Formation of Six-Membered Carbocycles 2.5 Cyclocarbopalladation with Formation of Seven-Membered Carbocycles 3 Formation of Heterocycles 3.1 Formation of Nitrogen Heterocycles 3.2 Formation of Oxygen Heterocycles 3.3 Formation of Sulfur Heterocycles 3.4 Formation of Silicon-Containing Heterocycles 4 Conclusion

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“…Alkyl chloride units, especially polychlorinated hydrocarbons, are a very important class of functional groups, which are widely found in bioactive molecules such as pharmaceuticals and pesticides [1] . Simultaneously, polychlorinated hydrocarbons units also can further transformed into a variety of new compounds, including aldehyde, [2a–d] ester, [2e–h] ketone, [2i–n] carboxylic acid, [2o–r] alkene, [2s–t] carbene, [2u–x] etc [2y–z] . Therefore, the formation of polychlorinated alkane units have been well established over the past few decades.…”

Section: Introductionmentioning

confidence: 99%

Recent Developments in the Polychloroalkylation by Use of Simple Alkyl Chlorides

Liang

Ouyang

et al. 2020

Adv Synth Catal

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Owing to their easy availability and cheapness, simple alkyl chlorides are good raw materials for introducing complex polychlorinated groups. Polychlorinated hydrocarbons units, such as di‐ or trichloromethyl groups, not only widely found in pesticide and bioactive molecule, but also can be as a precursor to converted into different functional groups such as −COOH, −CHO and −CO. The direct polychloroalkylation reaction by using simple alkyl chlrides has been considered to be an important tool for synthesizing complex polychlorinated compounds. This review summarizes recent developments, especially free radical strategies, in the polychloroalkylation of different substrates (such as 2‐acylpyridines, benzyl tertiary amines, alkenes, imine and 1,n‐enynes). We hope that this review provides a new perspective on this field and also provides a reference to develop environmentally friendly and sustainable methods.

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Palladium-Catalyzed Heck-type Domino Cyclization and Carboxylation to Synthesize Carboxylic Acids by Utilizing Chloroform as the Carbon Monoxide Source

Cited by 64 publications

References 73 publications

Dppf‐Ligated Palladium Complex as an Efficient Catalyst for the Synthesis of Biaryl Ketones Using Co₂(CO)₈ as a C1 Source with High TON and TOF

Dppf‐Ligated Palladium Complex as an Efficient Catalyst for the Synthesis of Biaryl Ketones Using Co₂(CO)₈ as a C1 Source with High TON and TOF

Cyclocarbopalladation as a Key Step in Cascade Reactions: Recent Developments

Recent Developments in the Polychloroalkylation by Use of Simple Alkyl Chlorides

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Palladium-Catalyzed Heck-type Domino Cyclization and Carboxylation to Synthesize Carboxylic Acids by Utilizing Chloroform as the Carbon Monoxide Source

Cited by 64 publications

References 73 publications

Dppf‐Ligated Palladium Complex as an Efficient Catalyst for the Synthesis of Biaryl Ketones Using Co2(CO)8 as a C1 Source with High TON and TOF

Dppf‐Ligated Palladium Complex as an Efficient Catalyst for the Synthesis of Biaryl Ketones Using Co2(CO)8 as a C1 Source with High TON and TOF

Cyclocarbopalladation as a Key Step in Cascade Reactions: Recent Developments

Recent Developments in the Polychloroalkylation by Use of Simple Alkyl Chlorides

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Dppf‐Ligated Palladium Complex as an Efficient Catalyst for the Synthesis of Biaryl Ketones Using Co₂(CO)₈ as a C1 Source with High TON and TOF

Dppf‐Ligated Palladium Complex as an Efficient Catalyst for the Synthesis of Biaryl Ketones Using Co₂(CO)₈ as a C1 Source with High TON and TOF