B-H and O-H bonds activation via a single electron transfer of frustrated radical pairs

被引：6

作者：

Pan, Yanlin ^{[1
]}

Cui, Jie ^{[1
]}

Wei, Yongliang ^{[1
]}

Xu, Zhaochao ^{[1
,2
]}

Wang, Tongdao ^{[1
]}

机构：

[1] Dalian Univ Technol, Zhang Dayu Sch Chem, Dalian 116024, Peoples R China

[2] Chinese Acad Sci, Dalian Inst Chem Phys, CAS Key Lab Separat Sci Analyt Chem, Dalian 116023, Peoples R China

来源：

DALTON TRANSACTIONS | 2021年 / 50卷 / 25期

基金：

中国国家自然科学基金;

关键词：

LEWIS PAIR; B(C6F5)(3)-CATALYZED HYDROSILATION; HYDROBORATION; BORANE; REACTIVITY; REDUCTION; MECHANISM; OXIDATION; BIS(PENTAFLUOROPHENYL)BORANE; H2O-CENTER-DOT-B(C6F5)(3);

D O I：

10.1039/d1dt01169c

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The rare examples of B-H bond activation in a frustrated radical pair regime have been observed by treatment of TEMPO radicals with Piers' borane HB(C6F5)(2) or bis-borane, respectively. The resulting concomitant formation of zwitterionic products and geminal N/B frustrated Lewis pairs implied a one electron process. In addition, the reaction of a TEMPO/B(C6F5)(3) pair with H2O center dot B(C6F5)(3) was assumed to involve one-electron reduction of water. Our results provide insights into chemical bond (e.g. B-H and O-H) activation via a single electron transfer.

引用

页码：8947 / 8954

页数：8

共 56 条

[1] Aqua, alcohol, and acetonitrile adducts of tris(perfluorophenyl)borane: Evaluation of Bronsted acidity and ligand lability with experimental and computational methods [J].

Bergquist, C ;

Bridgewater, BM ;

Harlan, CJ ;

Norton, JR ;

Friesner, RA ;

Parkin, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (43) :10581-10590

[2] 1H and 19F NMR investigation of the reaction of B(C6F5)3 with water in toluene solution [J].

Beringhelli, T ;

Maggioni, D ;

D'Alfonso, G .

ORGANOMETALLICS, 2001, 20 (23) :4927-4938

[3] Mechanistic studies on selectivity in the B(C6F5)3-catalyzed allylstannation of aldehydes:: Is hypercoordination at boron responsible? [J].

Blackwell, JM ;

Piers, WE ;

Parvez, M .

ORGANIC LETTERS, 2000, 2 (05) :695-698

[4] B(C6F5)3-catalyzed hydrosilation of imines via silyliminium intermediates [J].

Blackwell, JM ;

Sonmor, ER ;

Scoccitti, T ;

Piers, WE .

ORGANIC LETTERS, 2000, 2 (24) :3921-3923

[5] New Insights in Frustrated Lewis Pair Chemistry with Azides [J].

Boom, Devin H. A. ;

Jupp, Andrew R. ;

Nieger, Martin ;

Ehlers, Andreas W. ;

Slootweg, J. Chris .

CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (58) :13299-13308

[6]

CHOUKROUN R, 2006, ORGANOMETALLICS, V25

[7] Triple-decker main group cations [J].

Cowley, AH ;

Macdonald, CLB ;

Silverman, JS ;

Gorden, JD ;

Voigt, A .

CHEMICAL COMMUNICATIONS, 2001, (02) :175-176

[8] Equilibria in the B(C6F5)3-H2O system:: synthesis and crystal structures of H2O•B(C6F5)3 and the anions [HOB(C6F5)3]- and [F5C6)3B(μ-OH)B(C6F5)3]- [J].

Danopoulos, AA ;

Galsworthy, JR ;

Green, MLH ;

Cafferkey, S ;

Doerrer, LH ;

Hursthouse, MB .

CHEMICAL COMMUNICATIONS, 1998, (22) :2529-2530

[9] Frustrated Radical Pairs: Insights from EPR Spectroscopy [J].

Dasgupta, Ayan ;

Richards, Emma ;

Melen, Rebecca L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (01) :53-65

[10] Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds [J].

Dasgupta, Ayan ;

Stefkova, Katarina ;

Babaahmadi, Rasool ;

Gierlichs, Lukas ;

Ariafard, Alireza ;

Melen, Rebecca L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (36) :15492-15496

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