Efficient one-pot synthesis of 2-aryldihydrobenzofuran

被引:12
作者
Pan, CF
Ma, ZX
Yu, J
Zhang, ZH
Hui, AL
Wang, ZY [1 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
关键词
one-pot synthesis; 2-aryldihydrobenzofuran; benzylation; intramolecular Ullmann coupling; chemoselectivity;
D O I
10.1055/s-2005-871940
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 2-aryldihydrobenzofuran derivatives were successfully synthesized from the corresponding carbonyl compounds and (2-bromobenzyl)trimethylsilane by the one-pot benzylation-substitution procedure.
引用
收藏
页码:1922 / 1926
页数:5
相关论文
共 30 条
[1]   Ambident effect of a p-sulfinyl group for the introduction of two carbon substituents to phenol rings:: A convergent synthesis of diverse benzofuran neolignans [J].
Akai, S ;
Morita, N ;
Iio, K ;
Nakamura, Y ;
Kita, Y .
ORGANIC LETTERS, 2000, 2 (15) :2279-2282
[2]   HIGHLY CHEMOSELECTIVE ADDITION OF (ORTHO-NITROBENZYL)SILANES TO NONENOLIZABLE ALDEHYDES [J].
BARTOLI, G ;
BOSCO, M ;
CARETTI, D ;
DALPOZZO, R ;
TODESCO, PE .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4381-4384
[3]   Flavonoids from Dalbergia louvelii and their antiplasmodial activity [J].
Beldjoudi, N ;
Mambu, L ;
Labaïed, M ;
Grellier, P ;
Ramanitrahasimbola, D ;
Rasoanaivo, P ;
Martin, MT ;
Frappier, F .
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (11) :1447-1450
[4]   A biomimetic approach to dihydrobenzofuran synthesis [J].
Benbow, JW ;
Katoch-Rouse, R .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (15) :4965-4972
[5]  
BENNETAU B, 1985, B SOC CHIM FR, P90
[6]   Dihydrobenzofuran synthesis by an anodic [3+2] cycloaddition of phenols and unactivated alkenes [J].
Chiba, K ;
Fukuda, M ;
Kim, S ;
Kitano, Y ;
Tada, M .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) :7654-7656
[7]   In vitro antiinflammatory effects of neolignan woorenosides from the rhizomes of Coptis japonica [J].
Cho, JY ;
Baik, KU ;
Yoo, ES ;
Yoshikawa, K ;
Park, MH .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (09) :1205-1209
[8]   ANHYDROUS TETRABUTYLAMMONIUM FLUORIDE - A MILD BUT HIGHLY EFFICIENT SOURCE OF NUCLEOPHILIC FLUORIDE-ION [J].
COX, DP ;
TERPINSKI, J ;
LAWRYNOWICZ, W .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (17) :3216-3219
[9]   Asymmetric reactions of 2-methoxy-1,4-benzoquinones with styrenyl systems: Enantioselective syntheses of 8-aryl-3-methoxybicyclo [4.2.0]oct-3-en-2,5-diones, 7-aryl-3-hydroxybicyclo[3.2.1]oct-3-en-2,8-diones, 2-aryl-6-methoxy-2,3-dihydrobenzofuran-5-ols, and pterocarpans [J].
Engler, TA ;
Letavic, MA ;
Iyengar, R ;
LaTessa, KO ;
Reddy, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2391-2405
[10]   Lewis acid-controlled regioselectivity in reactions of styrenyl systems with benzoquinone monoimides: New regioselective syntheses of substituted 2-aryl-2,3-dihydrobenzofurans, 2-aryl-2,3-dihydroindoles, and 2-arylindoles [J].
Engler, TA ;
Chai, WY ;
LaTessa, KO .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9297-9308