@article{yao_bhaumik_dhanalekshmi_ptaszek_rodriguez_lindsey_2007, title={Synthesis of porphyrins bearing 1-4 hydroxymethyl groups and other one-carbon oxygenic substituents in distinct patterns}, volume={63}, ISSN={["0040-4020"]}, DOI={10.1016/j.tet.2007.07.108}, abstractNote={Porphyrins that bear one-carbon oxygenic substituents (hydroxymethyl, formyl, ester) directly attached to the macrocycle afford a compact architecture of utility for diverse applications. Routes to 9 porphyrins bearing such groups in distinct architectures (A4-, trans-A2-, trans-A2B2-, trans-AB-, and trans-AB2C-porphyrins) have been explored (A=hydroxymethyl), including porphyrins bearing two one-carbon units in different oxidation states (hydroxymethyl/ester, formyl/ester). The hydroxymethyl group was introduced via TBDMS-protected dipyrromethane precursors.}, number={43}, journal={TETRAHEDRON}, author={Yao, Zhen and Bhaumik, Jayeeta and Dhanalekshmi, Savithri and Ptaszek, Marcin and Rodriguez, Phillip A. and Lindsey, Jonathan S.}, year={2007}, month={Oct}, pages={10657–10670} } @misc{lindsey_dhanalekshmi_laha_taniguchi_2006, title={Scalable synthesis of dipyrromethanes}, volume={7,022,862}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Lindsey, J. S. and Dhanalekshmi, S. and Laha, J. K. and Taniguchi, M.}, year={2006} } @article{fan_taniguchi_yao_dhanalekshmi_lindsey_2005, title={1,9-bis(N,N-dimethylaminomethyl)dipyrromethanes in the synthesis of porphyrins bearing one or two meso substituents}, volume={61}, ISSN={["0040-4020"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-25144489698&partnerID=MN8TOARS}, DOI={10.1016/j.tet.2005.08.028}, abstractNote={A synthesis of 5,15-disubstituted zinc-porphyrins has been developed that employs condensation of a 1,9-bis(N,N-dimethylaminomethyl)dipyrromethane+a dipyrromethane in refluxing ethanol containing zinc acetate followed by oxidation with DDQ. The N,N-dimethylaminomethylation of the dipyrromethane was achieved via Eschenmoser's reagent (N,N-dimethylmethyleneammonium iodide) in CH2Cl2 at room temperature. The synthesis is compatible with diverse substituents (e.g., alkyl, aryl, ester, acetal) and enables rapid synthesis of trans-AB-, A2-, and A-porphyrins. The synthesis of >40 zinc porphyrins has been surveyed; 13 zinc porphyrins were isolated in yields of 5–20% without detectable scrambling.}, number={43}, journal={TETRAHEDRON}, publisher={Elsevier BV}, author={Fan, DZ and Taniguchi, M and Yao, Z and Dhanalekshmi, S and Lindsey, JS}, year={2005}, month={Oct}, pages={10291–10302} } @article{laha_dhanalekshmi_taniguchi_ambroise_lindsey_2003, title={A scalable synthesis of meso-substituted dipyrromethanes}, volume={7}, ISSN={["1520-586X"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-0346735296&partnerID=MN8TOARS}, DOI={10.1021/op034083q}, abstractNote={A one-flask synthesis of meso-substituted dipyrromethanes has been refined. The procedure entails reaction of an aldehyde in 100 equiv of pyrrole as the solvent containing a mild Lewis acid (e.g., InCl3) at room temperature. Following removal and recovery of excess pyrrole, the dipyrromethane is obtained by crystallization. The procedure generates minimal waste and does not require aqueous/organic extraction, chromatography, or distillation. The procedure has been scaled linearly to obtain >100 g of 5-phenyldipyrromethane. The utility of various analytical methods for characterizing dipyrromethanes has been investigated.}, number={6}, journal={ORGANIC PROCESS RESEARCH & DEVELOPMENT}, publisher={American Chemical Society (ACS)}, author={Laha, JK and Dhanalekshmi, S and Taniguchi, M and Ambroise, A and Lindsey, JS}, year={2003}, pages={799–812} }