Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 3-Boryl-2,1-borazaronaphthalene: Umpolung Reagents for Diversifying Naphthalene Isosteres.

Literature DB >> 29989812

3-Boryl-2,1-borazaronaphthalene: Umpolung Reagents for Diversifying Naphthalene Isosteres.

Jordan S Compton¹, Borna Saeednia¹, Christopher B Kelly¹, Gary A Molander¹.

Abstract

A Pd-catalyzed Miyaura borylation of 3-bromo-2,1-borazaronaphthalenes is reported. This method allows the formation of umpolung reagents for subsequent Pd-mediated cross-coupling. Coupling of this nucleophilic partner with a variety of commercially available aryl- and heteroaryl halides allows facile and rapid diversification of these cores.

Entities: CellLine Chemical Disease Gene Species

Mesh：

Substances：

Year: 2018 PMID： 29989812 PMCID： PMC6097885 DOI： 10.1021/acs.joc.8b01197

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

17 in total

1. Organotrifluoroborates: Another Branch of the Mighty Oak.

Authors: Gary A Molander
Journal: J Org Chem Date: 2015-07-07 Impact factor: 4.354

Review 2. The State of the Art in Azaborine Chemistry: New Synthetic Methods and Applications.

Authors: Zachary X Giustra; Shih-Yuan Liu
Journal: J Am Chem Soc Date: 2018-01-17 Impact factor: 15.419

Review 3. Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors: Sylvain Darses; Jean-Pierre Genet
Journal: Chem Rev Date: 2007-12-21 Impact factor: 60.622

4. Organic chemistry. Nanomole-scale high-throughput chemistry for the synthesis of complex molecules.

Authors: Alexander Buitrago Santanilla; Erik L Regalado; Tony Pereira; Michael Shevlin; Kevin Bateman; Louis-Charles Campeau; Jonathan Schneeweis; Simon Berritt; Zhi-Cai Shi; Philippe Nantermet; Yong Liu; Roy Helmy; Christopher J Welch; Petr Vachal; Ian W Davies; Tim Cernak; Spencer D Dreher
Journal: Science Date: 2014-11-20 Impact factor: 47.728

5. Innocent BN bond substitution in anthracene derivatives.

Authors: H L van de Wouw; J Y Lee; M A Siegler; R S Klausen
Journal: Org Biomol Chem Date: 2016-03-28 Impact factor: 3.876

6. A convergent, modular approach to functionalized 2,1-borazaronaphthalenes from 2-aminostyrenes and potassium organotrifluoroborates.

Authors: Steven R Wisniewski; Courtney L Guenther; O Andreea Argintaru; Gary A Molander
Journal: J Org Chem Date: 2013-12-11 Impact factor: 4.354

7. Enantioselective synthesis of cyclic secondary amines through Mo-catalyzed asymmetric ring-closing metathesis (ARCM).

Authors: Sarah J Dolman; Richard R Schrock; Amir H Hoveyda
Journal: Org Lett Date: 2003-12-11 Impact factor: 6.005

8. Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with 1-alkenyl halides or triflates: convenient synthesis of unsymmetrical 1,3-dienes via the borylation-coupling sequence.

Authors: Jun Takagi; Kou Takahashi; Tatsuo Ishiyama; Norio Miyaura
Journal: J Am Chem Soc Date: 2002-07-10 Impact factor: 15.419

3-Boryl-2,1-borazaronaphthalene: Umpolung Reagents for Diversifying Naphthalene Isosteres.

1. Organotrifluoroborates: Another Branch of the Mighty Oak.

Review 2. The State of the Art in Azaborine Chemistry: New Synthetic Methods and Applications.

Review 3. Potassium organotrifluoroborates: new perspectives in organic synthesis.

4. Organic chemistry. Nanomole-scale high-throughput chemistry for the synthesis of complex molecules.

5. Innocent BN bond substitution in anthracene derivatives.

6. A convergent, modular approach to functionalized 2,1-borazaronaphthalenes from 2-aminostyrenes and potassium organotrifluoroborates.

7. Enantioselective synthesis of cyclic secondary amines through Mo-catalyzed asymmetric ring-closing metathesis (ARCM).

8. Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with 1-alkenyl halides or triflates: convenient synthesis of unsymmetrical 1,3-dienes via the borylation-coupling sequence.

9. Benzazaborinines as Novel Bioisosteric Replacements of Naphthalene: Propranolol as an Example.

10. Regioselective Diversification of 2,1-Borazaronaphthalenes: Unlocking Isosteric Space via C-H Activation.

1. Late-stage functionalization of BN-heterocycles.

2. Photoredox Catalysis Enables Access to N-Functionalized 2,1-Borazaronaphthalenes.

3. Selectivity in the Elaboration of Bicyclic Borazarenes.