Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides-reaction discovery using parallel microscale experimentation

被引：209

作者：

Dreher, Spencer D. ^{[1
,2
]}

Dormer, Peter G. ^{[1
,2
]}

Sandrock, Deidre L. ^{[3
]}

Molander, Gary A. ^{[3
]}

机构：

[1] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA

[2] Merck & Co Inc, Catalyt React Discovery & Dev Lab, Rahway, NJ 07065 USA

[3] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 29期

关键词：

D O I：

10.1021/ja8031423

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Microscale parallel experimentation was used to discover three catalyst systems capable of coupling secondary organotrifluoroborates with sterically and electronically demanding aryl chlorides and bromides. The ensuing results represent the first comprehensive study of alkylboron coupling to aryl chlorides and, in particular, using secondary alkylboron partners. A ligand-dependent beta-hydride elimination/reinsertion mechanism was implicated in the cross-coupling of more hindered substrates, leading to isomeric mixtures of coupled products in some cases.

引用

页码：9257 / +

页数：4

共 40 条

[31] OHE T, 1990, SYNLETT, P221
[32] Cobalt(diamine)-catalyzed cross-coupling reaction of alkyl halides with arylmagnesium reagents: Stereoselective constructions of arylated asymmetric carbons and application to total synthesis of AH13205
Ohmiya, H
Yorimitsu, H
Oshima, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) : 1886 - 1889
[33] Stille cross-couplings of unactivated secondary alkyl halides using monoorganotin reagents
Powell, DA
Maki, T
Fu, GC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (02) : 510 - 511
[34] Recent advances in organotrifluoroborates chemistry
Stefani, Helio A.
Cella, Rodrigo
Vieira, Adriano S.
[J]. TETRAHEDRON, 2007, 63 (18) : 3623 - 3658
[35] Hiyama reactions of activated and unactivated secondary alkyl halides catalyzed by a nickel/norephedrine complex
Strotman, Neil A.
Sommer, Stefan
Fu, Gregory C.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) : 3556 - 3558
[36] SUZUKI A, 2002, ORGANIC SYNTHESES VI, V3
[37] ALKYL GROUP ISOMERIZATION IN CROSS-COUPLING REACTION OF SECONDARY ALKYL GRIGNARD-REAGENTS WITH ORGANIC HALIDES IN PRESENCE OF NICKEL-PHOSPHINE COMPLEXES AS CATALYSTS
TAMAO, K
KISO, Y
SUMITANI, K
KUMADA, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (26) : 9268 - 9269
[38] Ruphos-mediated Suzuki cross-coupling of secondary alkyl trifluoroborates
van den Hoogenband, Adri
Lange, Jos H. M.
Terpstra, Jan Willem
Koch, Melle
Visser, Gerben M.
Visser, Martin
Korstanje, Ties J.
Jastrzebski, Johann T. B. H.
[J]. TETRAHEDRON LETTERS, 2008, 49 (26) : 4122 - 4124
[39] Synthesis of aromatic bisabolene natural products via palladium-catalyzed cross-couplings of organozinc reagents
Vyvyan, JR
Loitz, C
Looper, RE
Mattingly, CS
Peterson, EA
Staben, ST
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) : 2461 - 2468
[40] Use of deuterium labeling studies to determine the stereochemical outcome of palladium migrations during an asymmetric intermolecular heck reaction
Wheatley, Bronwen M. M.
Keay, Brian A.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19) : 7253 - 7259

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