Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP): Efficient Catalysts for the Cyanosilylation and Cyanocarbonation of Aldehydes and Ketones

被引：21

作者：

Matsukawa, Satoru ^{[1
]}

Sekine, Izumi ^{[1
]}

Iitsuka, Ayumi ^{[1
]}

机构：

[1] Ibaraki Univ, Fac Educ, Dept Sci Educ, Ibaraki 3108512, Japan

来源：

MOLECULES | 2009年 / 14卷 / 09期

关键词：

organocatalysis; cyanosilylaton; cyanohydrin carbonate; phosphines; cyanation; BAYLIS-HILLMAN REACTION; TRIMETHYLSILYL CYANIDE; ASYMMETRIC CYANATION; CYANOHYDRIN; CONVENIENT; ESTERS;

D O I：

10.3390/molecules14093353

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A variety of aldehydes and ketones were transformed to their corresponding cyanohydrin silyl ethers in good to excellent yields in the presence of 1-5 mol% of tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP). Cyanohydrin carbonates were also readily prepared using 5-10 mol% of TTMPP as an organocatalyst.

引用

页码：3353 / 3359

页数：7

共 50 条

[31] Stability and reactivity of ferrocenyl(2,4,6-trimethoxyphenyl)carbenium salts
Natsume, S
Kurihara, H
Yamaguchi, T
Erabi, T
Wada, M
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 574 (01) : 86 - 93
[32] Synthesis of Aryl(2,4,6-trimethoxyphenyl)iodonium Trifluoroacetate Salts
Carreras, Virginie
Sandtorv, Alexander H.
Stuart, David R.
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (02): : 1279 - 1284
[33] ADDITION OF ORGANOMAGNESIUM HALIDES TO 2,4,6-TRIMETHOXYPHENYL CYCLOPROPYL KETONE
BREUER, E
SAREL, S
SALAMON, R
BULLETIN OF THE RESEARCH COUNCIL OF ISRAEL, 1962, A 11 (01): : 12 - &
[34] Consecutive cross-coupling of o-phenylenedizinc compound with acyl and/or aryl halides in the presence of Pd(0)-tris(2,4,6-trimethoxyphenyl)phosphine
Saiga, A
Hossain, KM
Takagi, K
TETRAHEDRON LETTERS, 2000, 41 (23) : 4629 - 4632
[35] Methoxylation of Acyl Fluorides with Tris(2,4,6-trimethoxyphenyl)phosphine via C-OMe Bond Cleavage under Metal-Free Conditions
Wang, Xiu
Wang, Zhenhua
Ishida, Takumi
Nishihara, Yasushi
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (11): : 7526 - 7533
[36] Effect of carbonates/phosphates as nucleophilic catalysts in dimethylformamide for efficient cyanosilylation of aldehydes and ketones
Prakash, G. K. Surya
Vaghoo, Habiba
Panja, Chiradeep
Surampudi, Vijayalakshmi
Kultyshev, Roman
Mathew, Thomas
Olah, George A.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (09) : 3026 - 3030
[37] CRYSTAL-STRUCTURE, INFRARED AND P-31 NUCLEAR-MAGNETIC-RESONANCE STUDIES OF COMPLEXES OF TRIS(2,4,6-TRIMETHOXYPHENYL)PHOSPHINE WITH MERCURY(II) HALIDES
BAKER, LJ
BOWMAKER, GA
SKELTON, BW
WHITE, AH
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (21): : 3235 - 3240
[38] STRUCTURAL, FAR-IR, AND P-31 NMR-STUDIES OF 2-COORDINATE COMPLEXES OF TRIS(2,4,6-TRIMETHOXYPHENYL)PHOSPHINE WITH SILVER(I) HALIDES
BAKER, LJ
BOWMAKER, GA
CAMP, D
EFFENDY
HEALY, PC
SCHMIDBAUR, H
STEIGELMANN, O
WHITE, AH
INORGANIC CHEMISTRY, 1992, 31 (17) : 3656 - 3662
[39] SYNTHESIS AND STRUCTURE OF TETRAKIS(2,4,6-TRIMETHOXYPHENYL)DIVANADIUM(II) BIS(TETRAHYDROFURANATE)
COTTON, FA
LEWIS, GE
MOTT, GN
INORGANIC CHEMISTRY, 1983, 22 (03) : 560 - 561
[40] 6-(4-Bromophenyl)-2-ethoxy-4-(2,4,6-trimethoxyphenyl)nicotinonitrile
Chantrapromma, Suchada
Fun, Hoong-Kun
Suwunwong, Thitipone
Padaki, Mahesh
Isloor, Arun M.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2914 - U2311

← 1 2 3 4 5 →