A highly efficient synthesis of triisopropylsilyldifluorobromopropyne yields a versatile gem-difluoromethylene building block

被引：26

作者：

Wang, ZG ^{[1
]}

Hammond, GB ^{[1
]}

机构：

[1] Univ Massachusetts, Dept Chem & Biochem, N Dartmouth, MA 02747 USA

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 24期

关键词：

D O I：

10.1039/a907784g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Triisopropylsilyldifluorobromopropyne, readily prepared in excellent yield from the reaction of lithium triisopropylsilylacetylide with CF2Br2, provides a convenient entry into a functionalized CF2 synthon.

引用

页码：2545 / 2546

页数：2

共 20 条

[11] Ynolates from the reaction of lithiosilyldiazomethane with carbon monoxide. New ketenylation reactions [J].

Kai, H ;

Iwamoto, K ;

Chatani, N ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (32) :7634-7635

[12] TOTAL SYNTHESIS OF 7,7-DIFLUOROARACHIDONIC, 10,10-DIFLUOROARACHIDONIC, AND 13,13-DIFLUOROARACHIDONIC ACIDS [J].

KWOK, PY ;

MUELLNER, FW ;

CHEN, CK ;

FRIED, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (12) :3684-3692

[13] ELECTROCHEMICAL, NICKEL-CATALYZED REFORMATSKY REACTION WITH METHYL CHLORODIFLUOROACETATE [J].

MCHAREK, S ;

SIBILLE, S ;

NEDELEC, JY ;

PERICHON, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 401 (1-2) :211-215

[14] Some influences of fluorine in bioorganic chemistry [J].

OHagan, D ;

Rzepa, HS .

CHEMICAL COMMUNICATIONS, 1997, (07) :645-652

[15]

Percy JM, 1997, TOP CURR CHEM, V193, P131

[16] REACTIVITY OF THE PERHALOGENOALKANES CF2BRX (X=CL, BR) WITH NUCLEOPHILES .4. CONDENSATION WITH CARBANIONS [J].

RICO, I ;

CANTACUZENE, D ;

WAKSELMAN, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (04) :1063-1065

[17] SYNTHESIS OF PARTIALLY FLUORINATED ANALOGS OF (Z)-5-DECENYL ACETATE - PROBES FOR HYDROPHOBIC INTERACTION IN PHEROMONE RECEPTION [J].

SUN, WC ;

NG, CS ;

PRESTWICH, GD .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) :132-137

[18] SYNTHESIS OF 3,3-DIFLUORO-2-AZETIDINONES AND 2,3-DIDEOXY-2,2-DIFLUORO-3-AMINO-SUGARS THROUGH THE REFORMATSKY REACTION OF DIFLUOROACETATE WITH IMINE [J].

TAGUCHI, T ;

KITAGAWA, O ;

SUDA, Y ;

OHKAWA, S ;

HASHIMOTO, A ;

IITAKA, Y ;

KOBAYASHI, Y .

TETRAHEDRON LETTERS, 1988, 29 (41) :5291-5294

[19] Methods for the synthesis of gem-difluoromethylene compounds [J].

Tozer, MJ ;

Herpin, TF .

TETRAHEDRON, 1996, 52 (26) :8619-8683

[20] Electroreductive defluorination of trifluoromethyl ketones and trifluoroacetic acid derivatives [J].

Uneyama, K ;

Mizutani, G ;

Maeda, K ;

Kato, T .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6717-6723

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