Bryan M. Gatehouse

Bio: Bryan M. Gatehouse is an academic researcher from Monash University, Clayton campus. The author has contributed to research in topics: Crystal structure & Denticity. The author has an hindex of 21, co-authored 92 publications receiving 1346 citations.

Difunctionalization of Primary Aromatic Amines with Ethylene. Synthesis of μ-Arylnitrilobis(ethane-2,1-diyl)dimercury(II) Complexes. Crystal Structure of 2,4,6-Me3C6H2N(CH2CH2HgCl)2.

Abstract: Reaction of primary aromatic amines, mercuric acetate, and ethylene in tetrahydrofuran under pressure (ca. 40 atm) yields the organomercurials ArN(CH 2 CH 2 -HgOAc) 2 (Ar = Ph, 2-ClC 6 H 4 , 3-ClC 6 H 4 , or 4-ClC 6 H 4 ) or, after treatment of the crude products with sodium halide, ArN(CH 2 CH 2 HgX) 2 (Ar = 4-MeC 6 H 4 , 4-MeOC 6 H 4 , or 2,4,6-Me 3 C 6 H 2 , X = Cl; Ar = 2,4-Cl 2 C 6 H 3 , 2,6-Cl 2 C 6 H 3 , or 2,4,6-Br 3 C 6 H 2 , X = Br). The X-ray diffraction study of 2,4,6-Me 3 C 6 H 2 N(CH 2 CH 2 HgCl) 2 shows the molecules to have near linear C-Hg-Cl stereochemistry, and to be arranged in centrosymmetric dimers with weak Hg ··· Cl intermolecular bonding.

Palladium-catalyzed cross-coupling reactions in total synthesis.

Abstract: In studying the evolution of organic chemistry and grasping its essence, one comes quickly to the conclusion that no other type of reaction plays as large a role in shaping this domain of science than carbon-carbon bond-forming reactions. The Grignard, Diels-Alder, and Wittig reactions are but three prominent examples of such processes, and are among those which have undeniably exercised decisive roles in the last century in the emergence of chemical synthesis as we know it today. In the last quarter of the 20th century, a new family of carbon-carbon bond-forming reactions based on transition-metal catalysts evolved as powerful tools in synthesis. Among them, the palladium-catalyzed cross-coupling reactions are the most prominent. In this Review, highlights of a number of selected syntheses are discussed. The examples chosen demonstrate the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.

Cascade reactions in total synthesis.

Abstract: The design and implementation of cascade reactions is a challenging facet of organic chemistry, yet one that can impart striking novelty, elegance, and efficiency to synthetic strategies. The application of cascade reactions to natural products synthesis represents a particularly demanding task, but the results can be both stunning and instructive. This Review highlights selected examples of cascade reactions in total synthesis, with particular emphasis on recent applications therein. The examples discussed herein illustrate the power of these processes in the construction of complex molecules and underscore their future potential in chemical synthesis.

The Diels--Alder reaction in total synthesis.

Abstract: The Diels-Alder reaction has both enabled and shaped the art and science of total synthesis over the last few decades to an extent which, arguably, has yet to be eclipsed by any other transformation in the current synthetic repertoire. With myriad applications of this magnificent pericyclic reaction, often as a crucial element in elegant and programmed cascade sequences facilitating complex molecule construction, the Diels-Alder cycloaddition has afforded numerous and unparalleled solutions to a diverse range of synthetic puzzles provided by nature in the form of natural products. In celebration of the 100th anniversary of Alder's birth, selected examples of the awesome power of the reaction he helped to discover are discussed in this review in the context of total synthesis to illustrate its overall versatility and underscore its vast potential which has yet to be fully realized.