메뉴 건너뛰기




Volumn 10, Issue 5, 2008, Pages 977-980

Mild synthesis of organophosphorus compounds: Reaction of phosphorus-containing carbenoids with organoboranes

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; CARBENE; DRUG DERIVATIVE; ESTER; HYDROCARBON; METHANE; ORGANOPHOSPHORUS COMPOUND; PHOSPHORUS;

EID: 43549114357     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800085u     Document Type: Article
Times cited : (27)

References (39)
  • 1
    • 33947430499 scopus 로고    scopus 로고
    • Representative examples: (a) Blakemore, P. R.; Burge, M. S. J. Am. Chem. Soc. 2007, 729, 3068.
    • Representative examples: (a) Blakemore, P. R.; Burge, M. S. J. Am. Chem. Soc. 2007, 729, 3068.
  • 20
    • 58149185695 scopus 로고    scopus 로고
    • Typical Experimental Procedure. A flame-dried, 50 mL flask was purged with nitrogen and charged with diethyl (chloromethyl)phosphonate 4b (4.0 mmol, 746 mg, 1.0 equiv) and dry THF (20 mL, The solution was cooled below-90°C (liquid nitrogen/ethanol bath, and n-butyllitium (1.6 M solution in hexane, 2.5 mL, 4.0 mmol, 1.0 equiv) was added slowly by syringe followed by Bu 3B (1.0 M solution in diethyl ether, 4.0 mL, 1.0 equiv) in one portion. The reaction mixture was warmed slowly to room temperature and was quenched by addition of water. The resulting biphasic mixture was stirred at rellux lor 2 h. After being cooled to room temperature, the layers were separated, the aqueous phase was extracted with EtOAc (3 ×, the combined organic layers were dried with MgSO4, and solvents were removed in vacuo. Purification of the crude product by flash chromatography on silica gel (EtOAc/hexane 1:1. v/v) yielded diethyl pentylphosphonate 3b H 3.84 mmol, 800
    • 4, and solvents were removed in vacuo. Purification of the crude product by flash chromatography on silica gel (EtOAc/hexane 1:1. v/v) yielded diethyl pentylphosphonate 3b H (3.84 mmol, 800 mg, 96%). Additional details can be found in the Supporting Information.
  • 21
    • 58149182857 scopus 로고    scopus 로고
    • Detailed procedures for the preparation of the reagents 4 can be found in the Supporting Information.
    • Detailed procedures for the preparation of the reagents 4 can be found in the Supporting Information.
  • 24
    • 46149129231 scopus 로고    scopus 로고
    • Teulade, M. P.; Savignac, P.; Abouajouade, E.; Collignon, N. J. Organomet. Chem. 1986, 312. 283. See also ref 4b.
    • (c)Teulade, M. P.; Savignac, P.; Abouajouade, E.; Collignon, N. J. Organomet. Chem. 1986, 312. 283. See also ref 4b.
  • 27
    • 0032275043 scopus 로고    scopus 로고
    • For a review on phosphine- borane complexes, see
    • For a review on phosphine- borane complexes, see: Brunel. J. M.; Faure, B.; Maffci, M. Coord. Chem. Rev. 1998, 178-180, 665.
    • (1998) Coord. Chem. Rev , vol.178-180 , pp. 665
    • Brunel, J.M.1    Faure, B.2    Maffci, M.3
  • 33
    • 0027761901 scopus 로고    scopus 로고
    • For references on the conversion of C-B into C-I, sec: (a) Montchamp, J.-L.; Migaud, M. E.; Frost. J. W. J. Org. Chem. 1993, 58, 7679.
    • For references on the conversion of C-B into C-I, sec: (a) Montchamp, J.-L.; Migaud, M. E.; Frost. J. W. J. Org. Chem. 1993, 58, 7679.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.