Gold(III)-Catalyzed Tandem Reaction of Ketones with Phenols: Efficient and Highly Selective Synthesis of Functionalized 4H-Chromenes
Yunkui Liu; Jianqiang Qian; Shaojie Lou; Jie Zhu; Zhenyuan Xu; Journal of Organic Chemistry 75 (2010) 1309–1312; doi:10.1021/jo902619x

data_4025246
_publ_section_title
;
 Gold(III)-Catalyzed Tandem Reaction of Ketones with Phenols: Efficient
 and Highly Selective Synthesis of Functionalized 4H-Chromenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1309
_journal_page_last               1312
_journal_paper_doi               10.1021/jo902619x
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         '2(C28 H24 O3), C H2 Cl2'
_chemical_formula_sum            'C57 H50 Cl2 O6'
_chemical_formula_weight         901.87
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.095(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.8992(11)
_cell_length_b                   10.2927(5)
_cell_length_c                   18.4191(9)
_cell_measurement_reflns_used    11406
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     4446.6(4)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(1)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rolling anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16282
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.9495
_exptl_absorpt_correction_T_min  0.9347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1896.0
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3889
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+3.8000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1549
_refine_ls_wR_factor_ref         0.1725
_reflns_number_gt                2547
_reflns_number_total             3889
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902619x_si_001.cif
_cod_data_source_block           jq221
_cod_original_cell_volume        4446.5(4)
_cod_database_code               4025246