Tin-free radical allylation of B-alkylcatecholboranes

被引：58

作者：

Schaffner, AP ^{[1
]}

Renaud, P ^{[1
]}

机构：

[1] Univ Bern, Dept Chem & Biochem, CH-3000 Bern 9, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 23期

关键词：

allylation; allylic compounds; boron; hydroboration; radical reactions; sulfones;

D O I：

10.1002/anie.200351171

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Organoboranes, prepared in situ by hydroboration of olefins with catecholborane, are efficiently allylated with allyl sulfones by a radical fragmentation process (see scheme). This hydroallylation of alkenes proved to be general for a wide range of alkenes and allyl sulfones.

引用

页码：2658 / 2660

页数：3

共 49 条

[1] THERMAL (1,3)-ALLYLIC REARRANGEMENTS IN SULFOXIDES AND SULFONES [J].

BAECHLER, RD ;

BENTLEY, P ;

DEURING, L ;

FISK, S .

TETRAHEDRON LETTERS, 1982, 23 (22) :2269-2272

[2] THERMAL AND PHOTOCHEMICAL FRAGMENTATION OF ALPHA-ALPHA-DIALKOXYBENZYL RADICALS - A COMPARISON OF THE THERMAL-REACTIONS WITH LASER-INDUCED FRAGMENTATIONS BY USING LASER FLASH AND LASER-JET PHOTOLYSES [J].

BANKS, JT ;

SCAIANO, JC ;

ADAM, W ;

OESTRICH, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (06) :2473-2477

[3] CYCLOPENTANATION WITH BETA-METHYLTHIO-ALLYL PHENYL SULFONE [J].

BARRE, V ;

UGUEN, D .

TETRAHEDRON LETTERS, 1987, 28 (48) :6045-6048

[4] α-Scission of sulfonyl radicals:: a versatile process for organic synthesis [J].

Bertrand, F ;

Le Guyader, F ;

Liguori, L ;

Ouvry, G ;

Quiclet-Sire, B ;

Seguin, S ;

Zard, SZ .

COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II FASCICULE C-CHIMIE, 2001, 4 (07) :547-555

[5]

Boudier A, 2000, CHEM-EUR J, V6, P2748, DOI 10.1002/1521-3765(20000804)6:15<2748::AID-CHEM2748>3.0.CO

[6]

2-Q

[7] Free-radical hydroxylation reactions of alkylboronates [J].

Cadot, C ;

Dalko, PI ;

Cossy, J ;

Ollivier, C ;

Chuard, R ;

Renaud, P .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7193-7202

[8] Radical carbon-carbon coupling reactions via organoboranes [J].

Cadot, C ;

Cossy, J ;

Dalko, PI .

CHEMICAL COMMUNICATIONS, 2000, (12) :1017-1018

[9] 2-functionalized allyl tris(trimethylsilyl)silanes as radical-based allylating agents [J].

Chatgilialoglu, C ;

Ferreri, C ;

Ballestri, M ;

Curran, DP .

TETRAHEDRON LETTERS, 1996, 37 (35) :6387-6390

[10] Tris(trimethylsilyl)silane as mediator in the radical-based allylation reactions of allyl and 2-functionalized allyl phenyl sulfones [J].

Chatgilialoglu, C ;

Alberti, A ;

Ballestri, M ;

Macciantelli, D ;

Curran, DP .

TETRAHEDRON LETTERS, 1996, 37 (35) :6391-6394

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