Zinc-catalyzed regioselective C-P coupling of p-quinol ethers with secondary phosphine oxides to afford 2-phosphinylphenols.
Zhang, Ming; Jia, Xiaoyu; Zhu, Haowei; Fang, Xutong; Ji, Chenyi; Zhao, Sizhuo; Han, Li-Biao; Shen, Ruwei; Organic & biomolecular chemistry 17 (2019) 2972–2984; doi:10.1039/c9ob00129h

data_7156696
_publ_section_title
;
 Zinc-catalyzed regioselective C-P coupling of p-quinol ethers with
 secondary phosphine oxides to afford 2-phosphinylphenols.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2972
_journal_page_last               2984
_journal_paper_doi               10.1039/c9ob00129h
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C27 H21 O2 P1'
_chemical_formula_sum            'C27 H21 O2 P'
_chemical_formula_weight         408.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-10-19 deposited with the CCDC.    2019-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 127.448(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.430(3)
_cell_length_b                   8.5473(14)
_cell_length_c                   20.666(3)
_cell_measurement_reflns_used    2625
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.20
_cell_volume                     2163.8(7)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15509
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.946
_diffrn_reflns_theta_min         1.662
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.849
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4300
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1196P)^2^+0.9256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1966
_refine_ls_wR_factor_ref         0.2242
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2876
_reflns_number_total             4500
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00129h2.cif
_cod_data_source_block           112
_cod_depositor_comments
'Adding full bibliography for 7156696--7156697.cif.'
_cod_original_formula_sum        'C27 H21 O2 P1'
_cod_database_code               7156696
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              54517