β-Carboline Amides as Intrinsic Directing Groups for C(sp2)-H Functionalization

被引：86

作者：

Viart, Helene M. -F. ^{[1
,2
]}

Bachmann, Andreas ^{[1
]}

Kayitare, William ^{[1
]}

Sarpong, Richmond ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

[2] Univ Calif San Francisco, Inst Neurodegenerat Dis, Sandler Neurosci Ctr, 675 Nelson Rising Lane, San Francisco, CA 94143 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 03期

基金：

美国国家科学基金会;

关键词：

C-H ALKYNYLATION; CATALYZED INTRAMOLECULAR AMINATION; UNACTIVATED C(SP(3))-H; BONDS; ARYLATION; DELTA; ALKYLATION; STRATEGY; SP(3); ALKENYLATION;

D O I：

10.1021/jacs.6b12569

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Many site-selective palladium-catalyzed C-H functionalization methods require directing groups. We report here beta-carboline amides as intrinsic directing groups for C(sp(2))-H functionalization. Various substrates including the natural product alangiobussinine and the marinacarboline core structure were functionalized using carboline-directed delta-C(sp(2))-H alkynylations. This transformation proceeds under mild conditions and is compatible with a wide variety of beta-arylethamines. delta-Alkynylation of beta-arylethamines via a six-membered palladacycle is favored over gamma-C(sp(2))-H bond functionalization when both positions are accessible. The versatility of beta-carboline amides as directing groups is evidenced by other delta-C(sp(2))-H functionalizations such as alkenylation, arylation, and C-N bond formation.

引用

页码：1325 / 1329

页数：5

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