New acyclic Pd–diaminocarbene catalyst for Suzuki arylation of meso-chlorosubstituted tricarboindocyanine dyes

Miltsov, Serguei; Karavan, V. S.; Boyarsky, Vadim P.; Pedro, Sara Gómez‐de; Alonso-Chamarro, Julián; Puyol, Mar

doi:10.1016/j.tetlet.2012.12.060

Cited by 37 publications

(6 citation statements)

References 24 publications

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“…Substitution at the meso‐position of heptamethine cyanine dyes can also be performed via the Suzuki cross‐coupling reaction with 4‐chlorophenylboronic acid ( 45 ), as shown in Scheme 12 [48] . In this procedure, an acyclic Pd‐diaminocarbene complex exhibited high catalytic activity in the Suzuki arylation of meso‐chlorine‐substituted tricarboindocyanine dyes 44 a – g .…”

Section: Synthesis Of Heptamethine Cyanine Dyesmentioning

confidence: 99%

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Near‐Infrared Fluorophores Based on Heptamethine Cyanine Dyes: From Their Synthesis and Photophysical Properties to Recent Optical Sensing and Bioimaging Applications

et al. 2022

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This review summarizes diverse synthetic methodologies to prepare a wide range of heptamethine cyanine dyes, including symmetrical, unsymmetrical, and meso‐substituted derivatives, and their photophysical properties and uses. Their sensing applications are also discussed, considering the nature of their electronic structures and photophysical properties. The optical sensing applications of these compounds can be potentially expanded via structural modification, broadening their absorption amplitude and spectral emission range from the ultraviolet to near‐infrared (NIR) region. In this review, several recent practical applications of the heptamethine cyanine dyes for ion and small molecule sensing, as well as bioimaging, are covered and discussed.

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Section: Synthesis Of Heptamethine Cyanine Dyesmentioning

confidence: 99%

“…This shows that the terminal amide group in 70 is located near the sulfur atom, allowing a rearrangement that possibly produces 71. Moreover, the formed thiol can attack another heptamethine cyanine dye (48) to form 72. The latter mechanism is believed to be responsible for the production of the active compounds used in this study.…”

Section: Bioimagingmentioning

confidence: 99%

Near‐Infrared Fluorophores Based on Heptamethine Cyanine Dyes: From Their Synthesis and Photophysical Properties to Recent Optical Sensing and Bioimaging Applications

et al. 2022

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“…(2) 2-溴丙二醛二苯胺缩合剂的合成(Ib-1) [14] . 取 (2) 染料 II-PHOH 的合成 (1,5-二 (1,1′-二乙基 -3,3,3′,3′-四甲基-3H-吲哚)-3-(4-羟基苯基)-二碳菁染料, 碘化盐) [15,16] [18] .…”

Section: 产品未经进一步纯化直接用于下一步反应unclassified

Pentamethine cyanine located in mitochondria: relationship between photostability and excited state lifetime

Huang¹,

Long²,

Li³

et al. 2017

Sci. Sin.-Chim

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“…The coupling of N -nucleophiles and isocyanides (C≡NR) is an important type of organic transformation yielding a great variety of chemical systems with newly formed C–N bonds [ 1 , 2 , 3 , 4 ]. In particular, these reactions represent an excellent route toward acyclic diaminocarbenes—an attractive alternative to N -heterocyclic carbene- and phosphine-based metal complexes used as catalysts in a number of important chemical processes [ 5 , 6 , 7 , 8 , 9 , 10 , 11 ], for example, Heck [ 12 , 13 ], Suzuki [ 12 , 14 ], Suzuki-Miyaura [ 13 , 15 , 16 , 17 ], and Sonogashira [ 13 , 18 , 19 ] cross-coupling reactions and some cyclizations/additions to substrates featuring C≡C and C=C bonds [ 20 , 21 , 22 , 23 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

Reaction between Indazole and Pd-Bound Isocyanides—A Theoretical Mechanistic Study

et al. 2018

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The mechanism of the addition of indazole (Ind)—a bifunctional aromatic N,NH-nucleophile—to cyclohexyl isocyanide coordinated to the palladium(II) center in the model complex cis-[PdCl2(CNMe)(CNCy)] (1) to give the corresponding aminocarbene ligand was investigated in detail by theoretical (DFT) methods. The most plausible mechanism of this reaction is that of the associative type involving nucleophilic attack of Ind by its unprotonated N atom at the isocyanide carbon atom followed by the stepwise proton transfer from the nucleophile molecule to the isocyanide N atom via deprotonation/protonation steps. Two reaction channels based on two tautomeric forms of indazole were found. The channel leading to the experimentally isolated aminocarbene product is based on the less stable tautomeric form. Another channel based on the more stable tautomer of Ind is slightly kinetically more favorable but it is endergonic. Thus, the regioselectivity of this reaction is thermodynamically rather than kinetically driven. The bonding situation in key species was analyzed.

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New acyclic Pd–diaminocarbene catalyst for Suzuki arylation of meso-chlorosubstituted tricarboindocyanine dyes

Cited by 37 publications

References 24 publications

Near‐Infrared Fluorophores Based on Heptamethine Cyanine Dyes: From Their Synthesis and Photophysical Properties to Recent Optical Sensing and Bioimaging Applications

Near‐Infrared Fluorophores Based on Heptamethine Cyanine Dyes: From Their Synthesis and Photophysical Properties to Recent Optical Sensing and Bioimaging Applications

Pentamethine cyanine located in mitochondria: relationship between photostability and excited state lifetime

Reaction between Indazole and Pd-Bound Isocyanides—A Theoretical Mechanistic Study

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