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Literature DB >> 24699913

The development of catalytic nucleophilic substitution reactions: challenges, progress and future directions.

Jie An¹, Ross M Denton, Tristan H Lambert, Eric D Nacsa.

Abstract

Bimolecular nucleophilic substitution reactions of alcohols are fundamentally important transformations in organic chemistry yet, to date, they are relatively underdeveloped with respect to catalysis. This Article describes the emerging area of catalytic SN2 reactions with specific emphasis on the design and development of phosphorus(V) and cyclopropenone-based catalytic SN2 reactions of alcohols.

Entities: Chemical Gene

Year: 2014 PMID： 24699913 DOI： 10.1039/c4ob00032c

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

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Cited

11 in total

1. Biphilic Organophosphorus Catalysis: Regioselective Reductive Transposition of Allylic Bromides via P(III)/P(V) Redox Cycling.

Authors: Kyle D Reichl; Nicole L Dunn; Nicholas J Fastuca; Alexander T Radosevich
Journal: J Am Chem Soc Date: 2015-04-21 Impact factor: 15.419

2. Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides.

Authors: Paul T Marcyk; Latisha R Jefferies; Deyaa I AbuSalim; Maren Pink; Mu-Hyun Baik; Silas P Cook
Journal: Angew Chem Int Ed Engl Date: 2019-01-15 Impact factor: 15.336

Review 3. Phosphine Organocatalysis.

Authors: Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal: Chem Rev Date: 2018-09-27 Impact factor: 60.622

4. A Biphilic Phosphetane Catalyzes N-N Bond-Forming Cadogan Heterocyclization via P^III/P^V═O Redox Cycling.

Authors: Trevor V Nykaza; Tyler S Harrison; Avipsa Ghosh; Rachel A Putnik; Alexander T Radosevich
Journal: J Am Chem Soc Date: 2017-05-10 Impact factor: 15.419

5. A front-face 'S_Ni synthase' engineered from a retaining 'double-S_N2' hydrolase.

Authors: Javier Iglesias-Fernández; Susan M Hancock; Seung Seo Lee; Maola Khan; Jo Kirkpatrick; Neil J Oldham; Katherine McAuley; Anthony Fordham-Skelton; Carme Rovira; Benjamin G Davis
Journal: Nat Chem Biol Date: 2017-06-12 Impact factor: 15.040

Review 6. Phosphorus-Based Catalysis.

Authors: Changmin Xie; Andrew J Smaligo; Xian-Rong Song; Ohyun Kwon
Journal: ACS Cent Sci Date: 2021-03-16 Impact factor: 14.553

The development of catalytic nucleophilic substitution reactions: challenges, progress and future directions.

1. Biphilic Organophosphorus Catalysis: Regioselective Reductive Transposition of Allylic Bromides via P(III)/P(V) Redox Cycling.

2. Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides.

Review 3. Phosphine Organocatalysis.

4. A Biphilic Phosphetane Catalyzes N-N Bond-Forming Cadogan Heterocyclization via P^III/P^V═O Redox Cycling.

5. A front-face 'S_Ni synthase' engineered from a retaining 'double-S_N2' hydrolase.

Review 6. Phosphorus-Based Catalysis.

7. Removal of Triphenylphosphine Oxide by Precipitation with Zinc Chloride in Polar Solvents.

8. Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic γ-umpolung addition-Wittig olefination.

9. Formamide catalyzed activation of carboxylic acids - versatile and cost-efficient amidation and esterification.

10. Mitsunobu Reactions Catalytic in Phosphine and a Fully Catalytic System.