Triethylborane-mediated hydrogallation and hydroindation: Novel access to organogalliums and organoindiums

被引：64

作者：

Takami, K ^{[1
]}

Mikami, S ^{[1
]}

Yorimitsu, H ^{[1
]}

Shinokubo, H ^{[1
]}

Oshima, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 17期

关键词：

D O I：

10.1021/jo0344790

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrogallation of carbon-carbon multiple bonds proceeds in the presence of triethylborane as a radical initiator. Several functionalities do not interfere with this reaction. Resulting alkenyl- and alkylgallium species can be trapped by several electrophiles. Highly regioselective radical addition of an indium hydride reagent to alkynes is also achieved. Various functionalities are tolerant under the reaction conditions. The reaction proceeds with complete anti stereoselectivity. Alkenylindiums obtained via hydroindation can be employed for the following cross-coupling reaction with aryl halides in one pot.

引用

页码：6627 / 6631

页数：5

共 49 条

[1] [Anonymous], 1991, REDUCTIONS ALUMINO B
[2] Araki S., 1988, APPL ORGANOMET CHEM, V2, P475
[3] BARRON AR, 1994, ENCY INORGANIC CHEM, V2, P1249
[4] ORGANOBORANES .37. SYNTHESIS AND PROPERTIES OF (Z)-1-ALKENYLBORONIC ESTERS
BROWN, HC
IMAI, T
[J]. ORGANOMETALLICS, 1984, 3 (09) : 1392 - 1395
[5] IMPROVED SYNTHESIS OF CIS-ALKENYLBORANES
CAMPBELL, JB
MOLANDER, GA
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 156 (01) : 71 - 79
[6] Iodine transfer cyclization mediated by DIBAL-H/THF
Chakraborty, A
Marek, I
[J]. CHEMICAL COMMUNICATIONS, 1999, (23) : 2375 - 2376
[7] (Z)-(E) INTERCONVERSION OF OLEFINS BY THE ADDITION-ELIMINATION SEQUENCE OF THE (TMS)(3)SI. RADICAL
CHATGILIALOGLU, C
BALLESTRI, M
FERRERI, C
VECCHI, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) : 3826 - 3831
[8] CHOI JH, 1995, B KOR CHEM SOC, V16, P469
[9] CHOI JH, 1995, B KOR CHEM SOC, V16, P474
[10] CHOI JH, 1995, B KOR CHEM SOC, V16, P416

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