Metalated Heterocycles and Their Applications in Synthetic Organic Chemistry

Chinchílla, Rafael; Nájera, Carmén; Yus, Miguel

doi:10.1021/cr020101a

Cited by 337 publications

(148 citation statements)

References 1,201 publications

(1,249 reference statements)

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“…Directed ortho-metalation (DoM) [43][44][45] followed by borylation with trialkylborate provides another approach for the synthesis of pyridinylboronic acids and esters bearing Directed Metalation Groups (DMGs).…”

Section: The Synthesis Of Pyridinylboronic Acids and Esters By Directmentioning

confidence: 99%

Recent progress in the synthesis of pyridinylboronic acids and esters

Liu¹,

Milo²,

Lai

2013

Arkivoc

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Recent progress in the synthesis of (un)substituted pyridinylboronic acids and esters is reviewed. Five approaches to the synthesis of (un)substituted pyridinylboronic acids and esters are summarized: (1) halogen-metal exchange (HMe) and borylation, (2) metal-hydrogen exchange via directed ortho-metallation (DoM) followed by borylation, (3) palladium-catalyzed crosscoupling of halopyridines with tetraalkoxydiborane or dialkoxyhydroborane (4) iridium or rhodium catalyzed C-H or C-F borylation, and (5) exchange / borylation 2.1.1. The general procedure of halogen-metal (Li or Mg) exchange / borylation 2.1.2. The selectivity of halogen-metal (Li or Mg) exchange / borylation 2.1.3. The synthesis of 2-pyridinylboronic acids and esters by halogen-organometal (Li or Mg) exchange / borylation 2.1.4. The synthesis of pyridinediboronic acids via halogen-organotin (Sn) exchange / borylation 2.2. The synthesis of pyridinylboronic acids and esters by directed ortho-metalation (DoM) / borylation 2.2.1. The general procedure of directed ortho-metalation (DoM) / borylation 2.2.2. The selectivity of directed ortho-metalation (DoM) / borylation 2.3. The synthesis of pyridinylboronic acids and esters by palladium-catalyzed cross-coupling of halopyridines with tetraalkoxydiboron or dialkoxyhydroborane 2.4. The synthesis of pyridinylboronic acids and esters by iridium-or rhodium-catalyzed

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Section: The Synthesis Of Pyridinylboronic Acids and Esters By Directmentioning

confidence: 99%

Recent progress in the synthesis of pyridinylboronic acids and esters

Liu¹,

Milo²,

Lai

2013

Arkivoc

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“…Heterocyclic boronic acid derivatives are generally prepared by reaction of the corresponding organolithium derivatives with a trialkylborate, 1,4,199 although there are examples of catalytic borylation of heteroarenes using iridium 200 and rhodium complexes. 200,201 The formed organoboron derivatives are used mainly for palladium-catalyzed cross-coupling reactions (the so-called Suzuki-Miyaura reaction 166 ).…”

Section: Boron Heterocyclesmentioning

confidence: 99%

“…1,4 The introduction of a silylated group can be required for blocking determined ring positions towards further transformations, as well as for ipso-substitution reactions by electrophiles or for palladium-catalyzed cross-coupling reactions with organic halides (the so-called Hiyama coupling 166 ).…”

Section: Silicon Heterocyclesmentioning

confidence: 99%

“…N-Boc-Protected 2-pyrrolyldimetylsilanols, 258 as well as their indolyl, 259 thienyl 258 and furyl 1 analogues, have been obtained by 2-lithiation and trapping with dimethyldichlorosilane followed by hydrolysis, and have been used in palladium-catalyzed coupling reactions with aryl halides. An example of the use of this methodology is the coupling of the pyrrolylsilanol 138 with piodoanisole, where the starting silanol is treated previously with sodium hydride generating the corresponding sodium silanolate, which is the real species that couples with the aryl halide to give compound 139 (Scheme 42).…”

Section: Aromatic Five-membered Ringsmentioning

confidence: 99%

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Metalated Heterocycles in Organic Synthesis: Recent Applications

2007

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“…1,2 A number of alternative approaches have therefore been developed for regioselective ortho-disubstitution, and lithiation followed by electrophilic substitution is one of the most recognized and efficient. [3][4][5][6][7][8][9][10][11][12][13][14][15][16] Directed lithiation of aromatic compounds 1 comprises deprotonation of a site ortho to a substituent that possesses a heteroatom (e.g. oxygen, nitrogen or sulfur) by use of a base.…”

Section: Introductionmentioning

confidence: 99%

Reactions of organolithium reagents with quinazoline derivatives

El‐Hiti¹,

Hegazy²,

Alotaibi³

et al. 2012

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This review deals with directed and regioselective lithiation of various quinazoline derivatives by the use of alkyllithiums in anhydrous THF at low temperature. Reactions of the lithium reagents obtained from the lithiation reactions with a range of electrophiles give the corresponding substituted derivatives in high yields. The procedures are simple, efficient and general to provide derivatives which might be difficult to produce by other means. In some cases nucleophilic addition of alkyllithiums takes place to produce the corresponding addition products via 1,2-and 3,4-additions. In other cases nucleophilic substitution or halogen-lithium exchange reactions occur.

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Metalated Heterocycles and Their Applications in Synthetic Organic Chemistry

Cited by 337 publications

References 1,201 publications

Recent progress in the synthesis of pyridinylboronic acids and esters

Recent progress in the synthesis of pyridinylboronic acids and esters

Metalated Heterocycles in Organic Synthesis: Recent Applications

Reactions of organolithium reagents with quinazoline derivatives

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