Synthesis of biaryls by intramolecular radical transfer in phosphinates

被引:44
作者
Clive, DLJ [1 ]
Kang, SZ [1 ]
机构
[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
关键词
D O I
10.1021/jo010371d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phosphinates 20a-35a give biaryls 20b-35b on heating with stannanes in the presence of AIBN. The process involves a radical ipso substitution on the migrating aryl ring.
引用
收藏
页码:6083 / 6091
页数:9
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共 77 条
[61]   REACTION OF TRIARYLMETHANOLS WITH LEAD TETRAACETATE MECHANISM OF LEAD TETRAACETATE OXIDATION OF MONOHYDRIC ALCOHOLS [J].
STARNES, WH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (07) :1807-&
[63]   PHENYLPHOSPHINIDENE OXIDE - THERMAL-DECOMPOSITION OF 2,3-BENZO-1,4,5,6,7-PENTAPHENYL-7-PHOSPHABICYCLO-[2.2.1]HEPT-5-ENE OXIDE [J].
STILLE, JK ;
FREEBURG.ME ;
HIGGINS, J ;
EICHELBE.JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (13) :4761-&
[64]   Stereoselective radical aryl migrations from sulfur to carbon [J].
Studer, A ;
Bossart, M .
CHEMICAL COMMUNICATIONS, 1998, (19) :2127-2128
[65]   Synthesis of biaryls by intramolecular radical aryl migration from silicon to carbon [J].
Studer, A ;
Bossart, M ;
Vasella, T .
ORGANIC LETTERS, 2000, 2 (07) :985-988
[66]   Stereoselective phenyl migration from silicon to carbon [J].
Studer, A ;
Bossart, M ;
Steen, H .
TETRAHEDRON LETTERS, 1998, 39 (48) :8829-8832
[67]   Factors influencing the course and mechanism of Grignard reactions XV The reaction of beta,beta-dimethylphenethyl chloride with phenylmagnesium bromide in the presence of cobaltous chloride [J].
Urry, WH ;
Kharasch, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :1438-1440
[68]   ENZYMATIC PREPARATION OF OPTICALLY-ACTIVE CYANOHYDRIN ACETATES [J].
VANALMSICK, A ;
BUDDRUS, J ;
HONICKESCHMIDT, P ;
LAUMEN, K ;
SCHNEIDER, MP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (18) :1391-1393
[69]   Intramolecular aryl migration from tin to carbon via a radical atom-transfer process [J].
Wakabayashi, K ;
Yorimitsu, H ;
Shinokubo, H ;
Oshima, K .
ORGANIC LETTERS, 2000, 2 (13) :1899-1901
[70]   Sodium p-toluenesulfinate/copper(II) acetate in free radical reactions of 5-aryl substituted alkenes [J].
Wang, SF ;
Chuang, CP ;
Lee, JH ;
Liu, ST .
TETRAHEDRON, 1999, 55 (08) :2273-2288