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Titolo:
A new facile approach to highly selective hydroboration of alkenes with sodium malonyloxyborohydride
Autore:
Huang, SW; Peng, WL; Shan, ZX; Zhao, DJ;
Indirizzi:
Wuhan Univ, Dept Chem, Wuhan 430072, Peoples R China Wuhan Univ Wuhan Peoples R China 430072 m, Wuhan 430072, Peoples R China
Titolo Testata:
NEW JOURNAL OF CHEMISTRY
fascicolo: 6, volume: 25, anno: 2001,
pagine: 869 - 871
SICI:
1144-0546(2001)25:6<869:ANFATH>2.0.ZU;2-K
Fonte:
ISI
Lingua:
ENG
Soggetto:
MOLECULAR ADDITION-COMPOUNDS; CARBOXYLIC-ACID MEDIA; BORANE ADDUCTS; BOROHYDRIDE; ORGANOBORANES; REDUCTION; KETONES; ESTERS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
22
Recensione:
Indirizzi per estratti:
Indirizzo: Huang, SW Wuhan Univ, Dept Chem, Wuhan 430072, Peoples R China Wuhan UnivWuhan Peoples R China 430072 30072, Peoples R China
Citazione:
S.W. Huang et al., "A new facile approach to highly selective hydroboration of alkenes with sodium malonyloxyborohydride", NEW J CHEM, 25(6), 2001, pp. 869-871

Abstract

The preparation and properties of sodium malonyloxyborohydride (SMB) are described. As a white solid, SMB is very sensitive to moisture in air. It isalso highly sensitive to the structure of alkenes. Thus SMB, prepared in situ from the reaction of malonic acid with equimolar NaBH4 in dry THF, hydroborates alkenes showing that terminal aliphatic alkenes undergo facile hydroboration with 98% of the boron moiety placed on the terminal position and2% at the 2 position. On the other hand, trisubstituted alkenes and cyclohexene show poor reactivity in the hydroboration as compared with terminal alkenes. These characteristics indicate that SMB is a highly regioselective monofunctional hydroborating reagent for terminal alkenes.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 20/09/20 alle ore 04:49:27