Facile synthesis of highly functionalized ethyltrifluoroborates

被引：17

作者：

Molander, Gary A. ^{[1
]}

Febo-Ayala, Wilma ^{[1
]}

Ortega-Guerra, Montserrat ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 15期

关键词：

D O I：

10.1021/jo800760f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Organotrifluoroborates are generating increased interest because of their ease of preparation and purification and indefinite shelf life. Herein we report the preparation of organotrifluoroborates bearing functional groups that can be manipulated at different stages of the synthetic route, exploiting the inertness of their carbon-boron bonds. The alkylation of 2,2-dicyanoethyltrifluoroborate with a variety of electrophiles and of (EWG)(2)CH2 with potassium iodomethyltrifluoroborate resulted in di- and trisubstituted ethyltrifluoroborates in good to excellent yields.

引用

页码：6000 / 6002

页数：3

共 22 条

[1] ORGANOBORANES .30. CONVENIENT PROCEDURES FOR THE SYNTHESIS OF ALKYLBORONIC AND ALKENYLBORONIC ACIDS AND ESTERS [J].

BROWN, HC ;

BHAT, NG ;

SOMAYAJI, V .

ORGANOMETALLICS, 1983, 2 (10) :1311-1316

[2] TRANSITION-METAL-PROMOTED HYDROBORATIONS OF ALKENES, EMERGING METHODOLOGY FOR ORGANIC TRANSFORMATIONS [J].

BURGESS, K ;

OHLMEYER, MJ .

CHEMICAL REVIEWS, 1991, 91 (06) :1179-1191

[3] Potassium organotrifluoroborates: New perspectives in organic synthesis [J].

Darses, Sylvain ;

Genet, Jean-Pierre .

CHEMICAL REVIEWS, 2008, 108 (01) :288-325

[4] Hydroboration of olefins with catecholborane at room temperature in the presence of N,N-dimethylacetamide [J].

Garrett, CE ;

Fu, GC .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3224-3225

[5] A facile synthesis of aryl iodides via potassium aryltrifluoroborates [J].

Kabalka, GW ;

Mereddy, AR .

TETRAHEDRON LETTERS, 2004, 45 (02) :343-345

[6] NICKEL-CATALYZED HYDROBORATION WITH CATECHOLBORANE [J].

KABALKA, GW ;

NARAYANA, C ;

REDDY, NK .

SYNTHETIC COMMUNICATIONS, 1994, 24 (07) :1019-1023

[7] SYNTHESIS OF 2-AMINO-3-BORONOPROPIONIC ACID - A BORON-CONTAINING ANALOG OF ASPARTIC-ACID [J].

KINDER, DH ;

AMES, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2452-2454

[8] CATALYTIC HYDROBORATION WITH RHODIUM COMPLEXES [J].

MANNIG, D ;

NOTH, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (10) :878-879

[9] Asymmetric alkyldifluoroboranes and their use in secondary amine synthesis [J].

Matteson, DS ;

Kim, GY .

ORGANIC LETTERS, 2002, 4 (13) :2153-2155

[10] BORONIC ESTERS IN STEREODIRECTED SYNTHESIS [J].

MATTESON, DS .

TETRAHEDRON, 1989, 45 (07) :1859-1885

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