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Literature DB >> 21405049

Reinvestigation of aminomethyltrifluoroborates and their application in Suzuki-Miyaura cross-coupling reactions.

Jessica Raushel¹, Deidre L Sandrock, Kanth V Josyula, Deborah Pakyz, Gary A Molander.

Abstract

A reinvestigation into the chemical composition of potassium aminomethyltrifluoroborates is reported. These trifluoroborato salts have been reassigned as zwitterionic ammoniomethyltrifluoroborates. Minor adjustments to the previously disclosed reaction conditions are reported that permit a similar level of activity as nucleophiles in Suzuki-Miyaura cross-coupling reactions.

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Year: 2011 PMID： 21405049 PMCID： PMC3074569 DOI： 10.1021/jo2001066

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

7 in total

1. Synthesis of amidomethyltrifluoroborates and their use in cross-coupling reactions.

Authors: Gary A Molander; Marie-Aude Hiebel
Journal: Org Lett Date: 2010-11-05 Impact factor: 6.005

2. Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated Stille coupling.

Authors: M S Jensen; C Yang; Y Hsiao; N Rivera; K M Wells; J Y Chung; N Yasuda; D L Hughes; P J Reider
Journal: Org Lett Date: 2000-04-20 Impact factor: 6.005

7. Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs).

Authors: Tomoya Shiro; Anne Schuhmacher; Moritz K Jackl; Jeffrey W Bode
Journal: Chem Sci Date: 2018-05-16 Impact factor: 9.825

7 in total

Reinvestigation of aminomethyltrifluoroborates and their application in Suzuki-Miyaura cross-coupling reactions.

1. Synthesis of amidomethyltrifluoroborates and their use in cross-coupling reactions.

2. Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated Stille coupling.

3. Synthesis of functionalized organotrifluoroborates via halomethyltrifluoroborates.

4. Scope of aminomethylations via Suzuki-Miyaura cross-coupling of organotrifluoroborates.

5. Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates.

6. Preparation of potassium alkoxymethyltrifluoroborates and their cross-coupling with aryl chlorides.

7. Aminomethylations via cross-coupling of potassium organotrifluoroborates with aryl bromides.

1. Cross-coupling of mesylated phenol derivatives with potassium alkoxymethyltrifluoroborates.

2. Suzuki-Miyaura cross-coupling of potassium trifluoro(N-methylheteroaryl)borates with aryl and heteroaryl halides.

3. Aminomethylation of Aryl Halides using α-Silylamines Enabled by Ni/Photoredox Dual Catalysis.

4. Rapid and efficient access to secondary arylmethylamines.

5. Synthesis and cross-coupling reactions of imidomethyltrifluoroborates with aryl chlorides.

6. Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4].

7. Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs).