Mechanochemical Solvent‐Free Suzuki–Miyaura Cross‐Coupling of Amides via Highly Chemoselective N−C Cleavage

Angewandte Chemie, Journal Year: 2021, Volume and Issue: 134(7)

Published: Dec. 8, 2021

Abstract Although cross‐coupling reactions of amides by selective N−C cleavage are one the most powerful and burgeoning areas in organic synthesis due to ubiquity amide bonds, development mechanochemical, solid‐state methods remains a major challenge. Herein, we report first mechanochemical strategy for highly chemoselective, solvent‐free palladium‐catalyzed bond activation. The method is conducted absence external heating, short reaction time shows excellent chemoselectivity σ functional group tolerance can be applied late‐stage functionalization complex APIs sequential orthogonal cross‐couplings exploiting double solventless methods. results extend environments advance chemical repertoire interconversions environmentally friendly

Language: Английский

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Recent trends and tactics in facile functionalization of neutral icosahedral carboranes (C2B10H12) and nido-carborane (7,8-C2B9H12−)

Advances in catalysis, Journal Year: 2022, Volume and Issue: unknown, P. 201 - 283

Published: Jan. 1, 2022

Language: Английский

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Synthesis of 3-Aryl-ortho-carboranes with Sensitive Functional Groups

Molecules, Journal Year: 2021, Volume and Issue: 26(23), P. 7297 - 7297

Published: Dec. 1, 2021

A simple and efficient method was developed for the one-pot synthesis of 3-aryl derivatives ortho-carborane with sensitive functional groups using 3-iodo-ortho-carborane aryl zinc bromides that were generated in situ. series 3-aryl-ortho-carboranes, including those containing nitrile ester groups, 3-RC6H4-1,2-C2B10H11 (R = p-Me, p-NMe2, p-OCH2OMe, p-OMe, o-CN, p-CN, o-COOEt, m-COOEt, p-COOEt) synthesized this approach. The solid-state structures p-CN) determined by single crystal X-ray diffraction. intramolecular hydrogen bonding involving ortho-substituents ring CH BH carborane discussed.

Language: Английский

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Palladium-catalyzed B7–11 penta-arylation of the {CB₁₁} monocarborane cluster

Chemical Communications, Journal Year: 2022, Volume and Issue: 59(1), P. 67 - 70

Published: Nov. 28, 2022

Regioselective, five-fold B-H activation of the monocarborane cluster [CB11H12]- at positions B7-11 has been accomplished. Selective substitution these by not reported before. Our protocol involves directing group assistance carboxylic acid functionality and is based on palladium catalysis using iodoarene coupling partners. Penta-arylated products are obtained in a single step with yields ranging from 42% to 89% good functional tolerance. X-Ray crystal structures for five new compounds confirm selective lower belt cage.

Language: Английский

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Palladium catalyzed selective arylation of B(4)-H of o-carboranes with potassium aryltrifluoroborate

Journal of Organometallic Chemistry, Journal Year: 2024, Volume and Issue: 1008, P. 123051 - 123051

Published: Feb. 26, 2024

Language: Английский

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