The preparation of a stable 2-pyridylboronate and its reactivity in the Suzuki–Miyaura cross-coupling reaction

Hodgson, Paul B.; Salingue, Fabrice H.

doi:10.1016/j.tetlet.2003.11.068

Cited by 117 publications

(49 citation statements)

References 20 publications

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“…The work by Fagnou and co-workers identified pyridine N-oxides as valuable surrogates to replace organometallic 2-pyridyl compounds [222] for the synthesis of 2-aryl pyridines. [223] Oxidation of the pyridine nitrogen dramatically increased the reactivity at the 2-position, thereby facilitating direct arylation as well as circumventing the need for prefunctionalization of one reaction partner.…”

Section: Metal-catalyzed C à H Activationmentioning

confidence: 99%

Chemoselectivity and the Curious Reactivity Preferences of Functional Groups

2009

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Achieving high levels of chemoselectivity has been the Achilles' heel of chemical synthesis. The excitement generated by the successful realization of chemoselective strategies underscores the painstaking efforts to define a set of conditions conducive to selection among the available reaction pathways. We discuss in this Review various aspects of chemoselectivity that have been addressed in a range of synthetic methods over the past decade. We have focused on the proposed mechanistic basis of the reactions under consideration in an attempt to categorize them and highlight the key concepts that have been emerging on the basis of these studies. Our overview of recent advances in chemoselective processes suggests that significant progress has been made, but a lot of challenges lie ahead.

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Section: Metal-catalyzed C à H Activationmentioning

confidence: 99%

Chemoselectivity and the Curious Reactivity Preferences of Functional Groups

2009

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“…Another way to suppress protodeboronation as a major side reaction is by using catalytic amounts of copper salts as additives [30]. While copper salts are often used as additives in Stille cross-coupling reactions, they are rarely utilized in Suzuki-Miyaura cross-coupling reactions [21a, 27, 30].…”

Section: Copper Salts As Additivesmentioning

confidence: 99%

State‐of‐the‐Art in Metal‐Catalyzed Cross‐Coupling Reactions of Organoboron Compounds with Organic Electrophiles

Lee

Hall

2013

Metal‐Catalyzed Cross‐Coupling Reactions and More

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“…2-Pyridinylboronic acids and esters using halogen-metal exchange (HMe) are generally synthesized from 2-bromopyridines (3, X = 2-Br). 5,6,13,17,[34][35][36][37][38][39][40][41][42] In the particular case of compound 3 (X = 2-I), 2-iodopyridine was used. 16 To improve the stability (particularly in air and water), pyridine-2-boronates such as 6, 34 7, 35,36 and 8 37,38 were developed.…”

Section: The Synthesis Of Pyridinylboronic Acids and Esters By Halogementioning

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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The preparation of a stable 2-pyridylboronate and its reactivity in the Suzuki–Miyaura cross-coupling reaction

Cited by 117 publications

References 20 publications

Chemoselectivity and the Curious Reactivity Preferences of Functional Groups

Chemoselectivity and the Curious Reactivity Preferences of Functional Groups

State‐of‐the‐Art in Metal‐Catalyzed Cross‐Coupling Reactions of Organoboron Compounds with Organic Electrophiles

Recent progress in the synthesis of pyridinylboronic acids and esters

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